JPS5771394A - Preparation of optically active monoalkyl beta-(s)-aminoglutarate - Google Patents

Preparation of optically active monoalkyl beta-(s)-aminoglutarate

Info

Publication number
JPS5771394A
JPS5771394A JP55146344A JP14634480A JPS5771394A JP S5771394 A JPS5771394 A JP S5771394A JP 55146344 A JP55146344 A JP 55146344A JP 14634480 A JP14634480 A JP 14634480A JP S5771394 A JPS5771394 A JP S5771394A
Authority
JP
Japan
Prior art keywords
aminoglutarate
group
monoalkyl
protecting group
beta
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.)
Granted
Application number
JP55146344A
Other languages
Japanese (ja)
Other versions
JPH0242476B2 (en
Inventor
Masaji Ono
Hamao Umezawa
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.)
SEIBUTSU KAGAKU KENKYUKAI
Microbial Chemistry Research Foundation
Original Assignee
SEIBUTSU KAGAKU KENKYUKAI
Microbial Chemistry Research Foundation
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 SEIBUTSU KAGAKU KENKYUKAI, Microbial Chemistry Research Foundation filed Critical SEIBUTSU KAGAKU KENKYUKAI
Priority to JP55146344A priority Critical patent/JPS5771394A/en
Priority to AT81108343T priority patent/ATE10835T1/en
Priority to EP81108343A priority patent/EP0050799B1/en
Priority to DE8181108343T priority patent/DE3167862D1/en
Publication of JPS5771394A publication Critical patent/JPS5771394A/en
Publication of JPH0242476B2 publication Critical patent/JPH0242476B2/ja
Granted legal-status Critical Current

Links

Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE: To obtain a compound, having an antimicrobial activity, and capable of being a synthetic intermediate for a β-lactam antibiotic, by treating a dialkyl β- protected aminoglutarate with an ester hydrolytic enzyme, and removing the protecting group of the amino group.
CONSTITUTION: A dialkyl β-protected aminoglutarate of formulaIhaving an easily removable protecting group (A), e.g., an aralkyloxycarbonyl group such as benzyl oxycarbonyl group, or tert-butoxycarbonyl group, is treated with an esterase to hydrolyze the pro-S alkyl group selectively and give a monoalkyl derivative. The resultant monoalkyl derivative is then catalytically reduced to remove the protecting group (A) and give a monoalkyl β-(S)-aminoglutarate of formula II. The methyl and ethyl esters have an antimicrobial acitivity against staphylococci. The resultant monoalkyl derivative can be easily converted into a synthetic intermediate for a carbapenem β-latcam.
COPYRIGHT: (C)1982,JPO&Japio
JP55146344A 1980-10-21 1980-10-21 Preparation of optically active monoalkyl beta-(s)-aminoglutarate Granted JPS5771394A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP55146344A JPS5771394A (en) 1980-10-21 1980-10-21 Preparation of optically active monoalkyl beta-(s)-aminoglutarate
AT81108343T ATE10835T1 (en) 1980-10-21 1981-10-15 PROCESS FOR THE PRODUCTION OF DI-ALKYLESTERS AND OPTICALLY ACTIVE MONO-ALKYLESTERS OF 3AMINOGLUTARS[URE.
EP81108343A EP0050799B1 (en) 1980-10-21 1981-10-15 New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid
DE8181108343T DE3167862D1 (en) 1980-10-21 1981-10-15 New processes for the production of di-alkyl esters and optically active mono-alkyl esters of 3-aminoglutaric acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP55146344A JPS5771394A (en) 1980-10-21 1980-10-21 Preparation of optically active monoalkyl beta-(s)-aminoglutarate

Publications (2)

Publication Number Publication Date
JPS5771394A true JPS5771394A (en) 1982-05-04
JPH0242476B2 JPH0242476B2 (en) 1990-09-21

Family

ID=15405574

Family Applications (1)

Application Number Title Priority Date Filing Date
JP55146344A Granted JPS5771394A (en) 1980-10-21 1980-10-21 Preparation of optically active monoalkyl beta-(s)-aminoglutarate

Country Status (1)

Country Link
JP (1) JPS5771394A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006075032A (en) * 2004-09-08 2006-03-23 Ube Ind Ltd Method for producing optically active (R or S) -3-aminoglutaric acid monoester compound
JP2010183917A (en) * 2010-06-01 2010-08-26 Ube Ind Ltd Method for producing optically active (r or s)-3-aminoglutaric acid monoester compound

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56127380A (en) * 1980-03-12 1981-10-06 Toyama Chem Co Ltd 2r,5r -3-oxo-7-oxo-1-azabicyclo 3,2,0 heptane-2-carboxylic acids and their preparations

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56127380A (en) * 1980-03-12 1981-10-06 Toyama Chem Co Ltd 2r,5r -3-oxo-7-oxo-1-azabicyclo 3,2,0 heptane-2-carboxylic acids and their preparations

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006075032A (en) * 2004-09-08 2006-03-23 Ube Ind Ltd Method for producing optically active (R or S) -3-aminoglutaric acid monoester compound
JP2010183917A (en) * 2010-06-01 2010-08-26 Ube Ind Ltd Method for producing optically active (r or s)-3-aminoglutaric acid monoester compound

Also Published As

Publication number Publication date
JPH0242476B2 (en) 1990-09-21

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