JPS6152159B2 - - Google Patents
Info
- Publication number
- JPS6152159B2 JPS6152159B2 JP56054865A JP5486581A JPS6152159B2 JP S6152159 B2 JPS6152159 B2 JP S6152159B2 JP 56054865 A JP56054865 A JP 56054865A JP 5486581 A JP5486581 A JP 5486581A JP S6152159 B2 JPS6152159 B2 JP S6152159B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- general formula
- formula
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005002 aryl methyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000008301 phosphite esters Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- -1 cephalosporin compound Chemical class 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cephalosporin Compounds (AREA)
Description
本発明は新規なアゼチジノン誘導体及びその製
造法に関する。
本発明のアゼチジノン誘導体は文献未載の新規
化合物であり、下記一般式〔〕で表わされる。
〔式中R1はアリールメチル基又はアリールオキシ
メチル基を示す。R2はハロゲン原子を置換基と
して有することのある低級アルキル基又はアリー
ルメチル基を示す。R3及びR4は同一又は異なつ
て低級アルキル基又はフエニル基を示す。〕
上記一般式〔〕で表わされるアゼチジノン誘
導体はペニシリン系、セフアロスポリン系抗生物
質を合成するための中間体として有用な化合物で
ある。例えば下記反応式に従い本発明の化合物か
ら抗菌剤として有用なセフアロスポリン系化合物
〔〕に誘導し得る。
〔式中R1、R2、R3及びR4は前記に同じ。〕
上記一般式〔〕で表わされるアゼチジノン誘
導体は種々の方法により製造されるが、その好ま
しい一例を挙げれば一般式
〔式中R1及びR2は前記に同じ。〕で表わされるア
ゼチジノン誘導体と一般式
〔式中R5は低級アルキル基又はフエニル基を示
す。R3及びR4は前記に同じ。〕で表わされる亜リ
ン酸エステルとを反応させることにより製造され
る。
本発明において、R1及びR2で示されるアリー
ルメチル基としては例えばベンジル基、ｐ−ヒド
ロキシベンジル基、ｐ−クロルベンジル基、ｐ−
ニトロベンジル基、ｐ−メトキシベンジル基、ジ
フエニルメチル基等を挙げることができる。R1
で示されるアリールオキシメチル基としては例え
ばフエノキシメチル基、ｐ−ニトロフエノキシメ
チル基、ｐ−メトキシフエノキシメチル基等を挙
げることができる。R2で示されるハロゲン原子
を置換基として有することのある低級アルキル基
としては例えばメチル基、エチル基、ｎ−プロピ
ル基、イソプロピル基、ｎ−ブチル基、tert−ブ
チル基、２−クロロエチル基、２・２・２−トリ
クロロエチル基等を挙げるとができる。R3、R4
及びR5で示される低級アルキル基としては例え
ばメチル基、エチル基、ｎ−プロピル基、イソプ
ロピル基、ｎ−ブチル基等を挙げることができ
る。
本発明において出発原料として用いられる一般
式〔〕で表わされるアゼチジノン誘導体は公知
の化合物であり、例えばテトラヘドロンレター
3001（1973）に記載の方法により容易に製造され
る。また一般式〔〕で表わされる亜リン酸エス
テルも入手容易な公知の化合物である。
一般式〔〕の化合物と一般式〔〕の化合物
との反応は無溶媒下又は適当な不活性溶媒中にて
行なわれる。不活性溶媒としては例えば塩化メチ
レン、クロロホルム、四塩化炭素、ジクロルエタ
ン等のハロゲン化炭化水素類、ジエチルエーテ
ル、ジブチルエーテル、ジオキサン、テトラヒド
ロフラン等のエーテル類、アセトニトリル、ブチ
ロニトリル等のニトリル類、ベンゼン、トルエ
ン、クロルベンゼン等の芳香族炭化水素類、ヘキ
サン、シクロヘキサン、ヘプタン、ペンタン等の
炭化水素類、これらの混合溶媒等を挙げることが
できる。一般式〔〕の化合物と一般式〔〕の
化合物との使用割合としては特に限定がなく広い
範囲内で適宜選択することができるが、通常前者
に対して後者を0.1〜10倍モル量、好ましくは1.5
〜３倍モル量程度用いるのがよい。該反応は室温
下、加温下及び冷却下のいずれでも行ない得る
が、常−20〜100℃にて行なわれる。
斯くして得られる本発明の化合物は通常行なわ
れている分離手段、例えば溶媒抽出、カラムクロ
マトグラフイー等の手段により反応混合物から容
易に単離精製される。
以下実施例を示すことによつて説明する。
実施例 １
化合物〔〕（R1＝フエノキシメチル、R2＝メ
チル）100mgをベンゼン１mlに溶解し、トリメチ
ルホスフアイト（化合物〔〕（R3、R4、R5＝メ
チル）0.45mlを加え、１時間加熱還流させる。反
応混合物を室温まで冷却し、酢酸エチル10mlで抽
出する。５％苛性ソーダ水溶液、飽和食塩水の順
序で洗浄した後、無水硫酸ナトリウムで乾燥す
る。減圧下溶媒を除去し、残渣をベンゼン−酢酸
エチル（１：１）の混合溶媒を用いて、シリカゲ
ルカラムで分離、精製すると、84.0mgの目的物
〔〕（R1＝フエノキシメチル、R2＝メチル、
R3、R4＝メチル）を得る。収率94％
IR（CHCl3、cm-1） 1782、1740、1685
NMR（CDCl3、δ）
1.90（ｓ、3H）、3.59（ｓ、3H）
3.75（ｓ、3H）、3.76（ｓ、3H）
4.52（ｓ、2H）、４・81（ｓ、1H）
5.02（ｓ、1H）、5.11（ｓ、1H）
5.48〜5.80（ｍ、2H）
6.8〜7.4（5H）、7.67（ｄ、1H）
実施例 ２〜13
原料及び反応条件を変化させ、操作、処理は実
施例１と同様に行つた。結果を第１〜４表に示
す。尚表中Phはフエニル基を意味する。
The present invention relates to a novel azetidinone derivative and a method for producing the same. The azetidinone derivative of the present invention is a novel compound that has not been described in any literature, and is represented by the following general formula []. [In the formula, R 1 represents an arylmethyl group or an aryloxymethyl group. R 2 represents a lower alkyl group or an arylmethyl group that may have a halogen atom as a substituent. R 3 and R 4 are the same or different and represent a lower alkyl group or a phenyl group. ] The azetidinone derivative represented by the above general formula [ ] is a compound useful as an intermediate for synthesizing penicillin and cephalosporin antibiotics. For example, a cephalosporin compound useful as an antibacterial agent can be derived from the compound of the present invention according to the following reaction formula. [In the formula, R 1 , R 2 , R 3 and R 4 are the same as above. ] The azetidinone derivative represented by the above general formula [ ] can be produced by various methods, but one preferred example is the azetidinone derivative represented by the general formula [In the formula, R 1 and R 2 are the same as above. ] Azetidinone derivatives and general formula [In the formula, R 5 represents a lower alkyl group or a phenyl group. R 3 and R 4 are the same as above. It is produced by reacting with a phosphite ester represented by ]. In the present invention, examples of the arylmethyl group represented by R 1 and R 2 include benzyl group, p-hydroxybenzyl group, p-chlorobenzyl group, p-
Examples include a nitrobenzyl group, p-methoxybenzyl group, and diphenylmethyl group. R 1
Examples of the aryloxymethyl group represented by the formula include phenoxymethyl group, p-nitrophenoxymethyl group, and p-methoxyphenoxymethyl group. Examples of the lower alkyl group represented by R 2 which may have a halogen atom as a substituent include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, 2-chloroethyl group, Examples include 2,2,2-trichloroethyl group. R3 , R4
Examples of the lower alkyl group represented by R5 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. The azetidinone derivatives represented by the general formula [ ] used as starting materials in the present invention are known compounds, such as tetrahedron letter
3001 (1973). Further, phosphorous acid ester represented by the general formula [] is also a well-known compound that is easily available. The reaction between the compound of general formula [] and the compound of general formula [] is carried out without a solvent or in a suitable inert solvent. Examples of inert solvents include halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, and dichloroethane, ethers such as diethyl ether, dibutyl ether, dioxane, and tetrahydrofuran, nitrites such as acetonitrile and butyronitrile, benzene, toluene, Examples include aromatic hydrocarbons such as chlorobenzene, hydrocarbons such as hexane, cyclohexane, heptane, and pentane, and mixed solvents thereof. The ratio of the compound of general formula [] to the compound of general formula [] is not particularly limited and can be appropriately selected within a wide range, but usually the latter is preferably 0.1 to 10 times the molar amount of the former. is 1.5
It is preferable to use about 3 times the molar amount. The reaction can be carried out at room temperature, heating or cooling, but is usually carried out at -20 to 100°C. The compound of the present invention thus obtained can be easily isolated and purified from the reaction mixture by conventional separation means such as solvent extraction and column chromatography. This will be explained below by showing examples. Example 1 100 mg of compound [] (R 1 = phenoxymethyl, R 2 = methyl) was dissolved in 1 ml of benzene, 0.45 ml of trimethyl phosphite (compound [] (R 3 , R 4 , R 5 = methyl) was added, and 1 Heat to reflux for an hour. Cool the reaction mixture to room temperature and extract with 10 ml of ethyl acetate. Wash with 5% aqueous sodium hydroxide solution and saturated brine in that order, and then dry over anhydrous sodium sulfate. Remove the solvent under reduced pressure and leave a residue. was separated and purified on a silica gel column using a mixed solvent of benzene-ethyl acetate (1:1) to obtain 84.0 mg of the target product [] (R 1 = phenoxymethyl, R 2 = methyl,
R 3 , R 4 = methyl) is obtained. Yield 94% IR (CHCl 3 , cm -1 ) 1782, 1740, 1685 NMR (CDCl 3 , δ) 1.90 (s, 3H), 3.59 (s, 3H) 3.75 (s, 3H), 3.76 (s, 3H ) 4.52 (s, 2H), 4.81 (s, 1H) 5.02 (s, 1H), 5.11 (s, 1H) 5.48-5.80 (m, 2H) 6.8-7.4 (5H), 7.67 (d, 1H) Examples 2 to 13 The operations and treatments were carried out in the same manner as in Example 1, except that the raw materials and reaction conditions were changed. The results are shown in Tables 1-4. In addition, Ph in the table means a phenyl group.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 14
化合物〔〕（R1＝ｐ−メトキシベンジル、R2
＝ｐ−クロルベンジル）と化合物〔〕（R3＝メ
チル、R4＝フエニル、R5＝メチル）を用いて実
施例１と同様の操作、処理を行つて、化合物
〔〕−(A)（R1＝ｐ−メトキシベンジル、R2＝ｐ
−クロルベンジル、R3＝メチル、R4＝フエニ
ル）と〔〕−(B)（R1＝ｐ−メトキシベンジル、
R2＝ｐ−クロルベンジル、R3＝メチル、R4＝メ
チル）を得た。〔〕−Ａの収率は54％、〔〕−Ｂ
の収率は32％であり、IR、NMRで確認同定し
た。
元素分析
〔〕−Ａ
理論値 Ｃ：56.49％ Ｈ：4.89％ Ｎ：4.25％
実測値 Ｃ：56.52％ Ｈ：4.88％ Ｎ：4.22％
〔〕−Ｂ
理論値 Ｃ：52.30％ Ｈ：5.07％ Ｎ：4.69％
実測値 Ｃ：52.28％ Ｈ：5.05％ Ｎ：4.73％
実施例 15
化合物〔〕（R1＝フエノキシメチル、R2＝ｐ
−ニトロベンジル）と化合物〔〕（R3、R4、R5
＝メチル）を用いて実施例１と同様の操作、処理
を行つて化合物〔〕（R1＝フエノキシメチル、
R2＝ｐ−ニトロベンジル、R3、R4＝メチル）を
得た。収率86％ IR、NMRで確認同定を行つ
た。
元素分析
理論値 Ｃ：50.59％ Ｈ：4.75％ Ｎ：7.08％
実測値 Ｃ：50.62％ Ｈ：4.76％ Ｎ：7.11％
実施例 16
化合物〔〕（R1＝ベンジル、R2＝ジフエニル
メチルと化合物〔〕（R3、R4、R5＝フエニル）
を用いて実施例１と同様の操作、処理を行つて化
合物〔〕（R1＝ベンジル、R2＝ジフエニルメチ
ル、R3、R4＝フエニル）を得た。収率84％
IR、NMRで確認同定した。
元素分析
理論値 Ｃ：67.19％ Ｈ：5.10％ Ｎ：3.82％
実測値 Ｃ：67.16％ Ｈ：5.10％ Ｎ：3.83％
実施例 17
化合物〔〕（R1＝ベンジル、R2＝ｔ−ブチ
ル）と化合物〔〕（R3、R4＝メチル、R5＝フエ
ニル）を用いて実施例１と同様の操作、処理を行
つて化合物〔〕（R1＝ベンジル、R2＝ｔ−ブチ
ル、R3、R4＝メチル）を得た。収率89.5％
IR、NMRで確認同定を行つた。
元素分析
理論値 Ｃ：52.99％ Ｈ：6.28％ Ｎ：5.62％
実測値 Ｃ：52.95％ Ｈ：6.30％ Ｎ：5.65％[Table] Example 14 Compound [] (R 1 = p-methoxybenzyl, R 2
= p-chlorobenzyl) and the compound [] (R 3 = methyl, R 4 = phenyl, R 5 = methyl) were subjected to the same operations and treatments as in Example 1 to obtain the compound []-(A) ( R 1 = p-methoxybenzyl, R 2 = p
-chlorobenzyl, R 3 = methyl, R 4 = phenyl) and []-(B) (R 1 = p-methoxybenzyl,
R2 =p-chlorobenzyl, R3 =methyl, R4 =methyl) were obtained. The yield of []-A is 54%, []-B
The yield was 32%, and the identification was confirmed by IR and NMR. Elemental analysis []-A Theoretical value C: 56.49% H: 4.89% N: 4.25% Actual value C: 56.52% H: 4.88% N: 4.22% []-B Theoretical value C: 52.30% H: 5.07% N: 4.69% Actual value C: 52.28% H: 5.05% N: 4.73% Example 15 Compound [] (R 1 = phenoxymethyl, R 2 = p
-nitrobenzyl) and the compound [] (R 3 , R 4 , R 5
= methyl), the same operations and treatments as in Example 1 were performed to obtain the compound [] (R 1 = phenoxymethyl,
R2 =p-nitrobenzyl, R3 , R4 =methyl) was obtained. Yield: 86% Confirmation and identification were performed by IR and NMR. Elemental analysis Theoretical value C: 50.59% H: 4.75% N: 7.08% Actual value C: 50.62% H: 4.76% N: 7.11% Example 16 Compound [] (R 1 = benzyl, R 2 = diphenylmethyl and compound [] (R 3 , R 4 , R 5 = phenyl)
The same operations and treatments as in Example 1 were performed using the following to obtain a compound [] (R 1 = benzyl, R 2 = diphenylmethyl, R 3 , R 4 = phenyl). Yield: 84% Confirmed and identified by IR and NMR. Elemental analysis Theoretical value C: 67.19% H: 5.10% N: 3.82% Actual value C: 67.16% H: 5.10% N: 3.83% Example 17 Compound [] (R 1 = benzyl, R 2 = t-butyl) Compound [] (R 3 , R 4 = methyl, R 5 = phenyl) was subjected to the same operations and treatments as in Example 1 to obtain compound [] (R 1 = benzyl, R 2 = t-butyl, R 3 , R 4 =methyl). Yield: 89.5% Confirmation and identification were performed by IR and NMR. Elemental analysis Theoretical value C: 52.99% H: 6.28% N: 5.62% Actual value C: 52.95% H: 6.30% N: 5.65%
Claims (1)
メチル基を示す。R2はハロゲン原子を置換基と
して有することのある低級アルキル基又はアリー
ルメチル基を示す。R3及びR4は同一又は異なつ
て低級アルキル基又はフエニル基を示す。〕 で表わされるアゼチジノン誘導体。 ２ 一般式 〔式中R1はアリールメチル基又はアリールオキシ
メチル基を示す。R2はハロゲン原子を置換基と
して有することのある低級アルキル基又はアリー
ルメチル基を示す。〕 で表わされるアゼチジノン誘導体と一般式 〔式中R3、R4及びR5は同一又は異なつて低級アル
キル基又はフエニル基を示す。〕 で表わされる亜リン酸エステルとを反応させて一
般式 〔式中R1、R2、R3及びR4は前記に同じ。〕 で表わされるアゼチジノン誘導体を得ることを特
徴とするアゼチジノン誘導体の製造法。[Claims] 1. General formula [In the formula, R 1 represents an arylmethyl group or an aryloxymethyl group. R 2 represents a lower alkyl group or an arylmethyl group that may have a halogen atom as a substituent. R 3 and R 4 are the same or different and represent a lower alkyl group or a phenyl group. ] Azetidinone derivative represented by. 2 General formula [In the formula, R 1 represents an arylmethyl group or an aryloxymethyl group. R 2 represents a lower alkyl group or an arylmethyl group that may have a halogen atom as a substituent. ] Azetidinone derivative and general formula represented by [In the formula, R 3 , R 4 and R 5 are the same or different and represent a lower alkyl group or a phenyl group. ] By reacting with a phosphite ester represented by the general formula [In the formula, R 1 , R 2 , R 3 and R 4 are the same as above. ] A method for producing an azetidinone derivative, the method comprising obtaining an azetidinone derivative represented by:
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56054865A JPS57169499A (en) | 1981-04-10 | 1981-04-10 | Azetidinone derivative and its preparation |
| GB8209646A GB2099817B (en) | 1981-04-10 | 1982-04-01 | Azetidinone derivatives and process for the preparation of the same |
| FR8206164A FR2509300B1 (en) | 1981-04-10 | 1982-04-08 | AZETIDINONE DERIVATIVES AND PROCESS FOR THEIR PREPARATION |
| DE19823213264 DE3213264A1 (en) | 1981-04-10 | 1982-04-08 | NEW AZETIDINONE COMPOUNDS AND METHOD FOR THE PRODUCTION THEREOF |
| US06/865,651 US4689411A (en) | 1981-04-10 | 1986-05-15 | 4-thio azetidinone intermediates and process for the preparation of the same |
| US07/071,664 US4784734A (en) | 1981-04-10 | 1987-07-09 | Azetidinone derivatives and process for the preparation of the same |
| US07/166,918 US4853468A (en) | 1981-04-10 | 1988-03-11 | Process for the preparation of cephem derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56054865A JPS57169499A (en) | 1981-04-10 | 1981-04-10 | Azetidinone derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57169499A JPS57169499A (en) | 1982-10-19 |
| JPS6152159B2 true JPS6152159B2 (en) | 1986-11-12 |
Family
ID=12982477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56054865A Granted JPS57169499A (en) | 1981-04-10 | 1981-04-10 | Azetidinone derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57169499A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6240458U (en) * | 1985-08-29 | 1987-03-11 | ||
| JPH0532961U (en) * | 1991-10-08 | 1993-04-30 | 松下電器産業株式会社 | Electric kotatsu with fan function |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2099817B (en) * | 1981-04-10 | 1985-05-15 | Otsuka Kagaku Yakuhin | Azetidinone derivatives and process for the preparation of the same |
-
1981
- 1981-04-10 JP JP56054865A patent/JPS57169499A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6240458U (en) * | 1985-08-29 | 1987-03-11 | ||
| JPH0532961U (en) * | 1991-10-08 | 1993-04-30 | 松下電器産業株式会社 | Electric kotatsu with fan function |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57169499A (en) | 1982-10-19 |
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