JPS565457A - Thienamycin intermediate - Google Patents

Thienamycin intermediate

Info

Publication number
JPS565457A
JPS565457A JP8097379A JP8097379A JPS565457A JP S565457 A JPS565457 A JP S565457A JP 8097379 A JP8097379 A JP 8097379A JP 8097379 A JP8097379 A JP 8097379A JP S565457 A JPS565457 A JP S565457A
Authority
JP
Japan
Prior art keywords
formula
hydroxyethyl
thienamycin
azetidinone
prepare
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.)
Pending
Application number
JP8097379A
Other languages
Japanese (ja)
Inventor
Tetsuji Kametani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daiichi Pharmaceutical Co Ltd
Original Assignee
Daiichi Pharmaceutical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Daiichi Pharmaceutical Co Ltd filed Critical Daiichi Pharmaceutical Co Ltd
Priority to JP8097379A priority Critical patent/JPS565457A/en
Publication of JPS565457A publication Critical patent/JPS565457A/en
Pending legal-status Critical Current

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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

NEW MATERIAL:A 3-(1'-hydroxyethyl)-4-(β,β-disubstituted ethyl)-2-azetidinone shown by the formula II (R1 is alkyl).
EXAMPLE: 3-(1'-Hydroxyethyl)-4-(β,β-dimethoxyethyl)-2-azetidinone.
USE: An intermediate for a novel antibiotic thienamycin [3-(2-aminoethylthio)-6-(1- hydroxyethyl)-7-oxo-1-azabicyclo(3,2,0)hepto-2-ene-2-carboxylic acid]. The use of ?the intermediate can prepare thienamycin industrially advantageously.
PROCESS: A 3-nitropropanaldimethylacetal shown by the formula III is reacted with a methyl crotonate shown by the formula IV (R2 and R3 are lower alkyl) to give an isoxazoline derivative shown by the formula V or VI, which is reduced under moderate pressure to prepare an amine derivative shown by the formula VII. This compound finally undergoes a Grignard reaction to give a compound shown by the formula II.
COPYRIGHT: (C)1981,JPO&Japio
JP8097379A 1979-06-27 1979-06-27 Thienamycin intermediate Pending JPS565457A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP8097379A JPS565457A (en) 1979-06-27 1979-06-27 Thienamycin intermediate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP8097379A JPS565457A (en) 1979-06-27 1979-06-27 Thienamycin intermediate

Publications (1)

Publication Number Publication Date
JPS565457A true JPS565457A (en) 1981-01-20

Family

ID=13733448

Family Applications (1)

Application Number Title Priority Date Filing Date
JP8097379A Pending JPS565457A (en) 1979-06-27 1979-06-27 Thienamycin intermediate

Country Status (1)

Country Link
JP (1) JPS565457A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS567759A (en) * 1979-07-02 1981-01-27 Dai Ichi Seiyaku Co Ltd Intermediate of descisdeaminothienamycin
JPS5659748A (en) * 1979-10-20 1981-05-23 Dai Ichi Seiyaku Co Ltd Intermediate of thienamycin

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5277084A (en) * 1975-11-21 1977-06-29 Merck & Co Inc Nn and carboxyl derivatives of thienamycine
JPS5334797A (en) * 1976-09-08 1978-03-31 Smithkline Corp 77acylaminoo88oxoo33oxaa 11azabicyclo *4*2*0* octanee 22carboxylic acid derivative
JPS5466696A (en) * 1977-10-19 1979-05-29 Merck & Co Inc 33substitutedd66*1**hydroxyethyl**77oxoo11 azabicyclo*3*2*0**heptoo22enee22carboxylic acid

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5277084A (en) * 1975-11-21 1977-06-29 Merck & Co Inc Nn and carboxyl derivatives of thienamycine
JPS5334797A (en) * 1976-09-08 1978-03-31 Smithkline Corp 77acylaminoo88oxoo33oxaa 11azabicyclo *4*2*0* octanee 22carboxylic acid derivative
JPS5466696A (en) * 1977-10-19 1979-05-29 Merck & Co Inc 33substitutedd66*1**hydroxyethyl**77oxoo11 azabicyclo*3*2*0**heptoo22enee22carboxylic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS567759A (en) * 1979-07-02 1981-01-27 Dai Ichi Seiyaku Co Ltd Intermediate of descisdeaminothienamycin
JPS5659748A (en) * 1979-10-20 1981-05-23 Dai Ichi Seiyaku Co Ltd Intermediate of thienamycin

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