FR2323680A1 - Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. - Google Patents

Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.

Info

Publication number
FR2323680A1
FR2323680A1 FR7528151A FR7528151A FR2323680A1 FR 2323680 A1 FR2323680 A1 FR 2323680A1 FR 7528151 A FR7528151 A FR 7528151A FR 7528151 A FR7528151 A FR 7528151A FR 2323680 A1 FR2323680 A1 FR 2323680A1
Authority
FR
France
Prior art keywords
aromatic
acid
prepd
substd
penicillins
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
FR7528151A
Other languages
French (fr)
Other versions
FR2323680B1 (en
Inventor
Yani Christidis
Alain Schouteete
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.)
Nobel Hoechst Chimie SA
Original Assignee
Nobel Hoechst Chimie SA
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 Nobel Hoechst Chimie SA filed Critical Nobel Hoechst Chimie SA
Priority to FR7528151A priority Critical patent/FR2323680A1/en
Priority to BE168798A priority patent/BE843994A/en
Priority to IT5093476A priority patent/IT1066142B/en
Priority to NL7609939A priority patent/NL7609939A/en
Priority to CH1141676A priority patent/CH614928A5/xx
Priority to CA260,800A priority patent/CA1066304A/en
Priority to DE19762640615 priority patent/DE2640615A1/en
Priority to JP51108725A priority patent/JPS5236644A/en
Priority to GB37651/76A priority patent/GB1520824A/en
Priority to US05/722,284 priority patent/US4105690A/en
Priority to SE7610065A priority patent/SE7610065L/en
Priority to SE7610064A priority patent/SE7610064L/en
Publication of FR2323680A1 publication Critical patent/FR2323680A1/en
Application granted granted Critical
Publication of FR2323680B1 publication Critical patent/FR2323680B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Abstract

The substd. N-acylated glycines Ar-CH(COOH)-NHCOR (I) are prepd. by the reaction of a carboxamide glycolic acid HOCH(COOH)-NHCOR (II) with an aromatic cpd. ArH (III), the reaction being effected in the presence of a strong mineral acid and a minimum of water (where Ar is an aromatic group which may be substd. and may have >=1 rings; R is (un)satd. alkyl, which may be substd). The prods are intermediates for the prepn. of semisynthetic penicillins. The process is general in its application, is simple to carry out, and gives good yields. Typically (III) is thiophene, benzene, phenol or 3,5-dihydroxy benzoic acid and R is methyl. In an example, 36.8g thiophene was treated with 65.2g (II hydrate, R-CO = acryloyl) in acetic acid/sulphyric acid contg. cupric acetate to give 50% yield of N-acryloyl thienylglycine, mpt. 140 degrees C.
FR7528151A 1975-09-12 1975-09-12 Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd. Granted FR2323680A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
FR7528151A FR2323680A1 (en) 1975-09-12 1975-09-12 Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.
BE168798A BE843994A (en) 1975-09-12 1976-07-09 PROCESS FOR MANUFACTURING N-ACYL DERIVATIVES OF GLYCINES & -SUBSTITUTED BY AROMATIC RADICALS AND NEW PRODUCTS RESULTING
IT5093476A IT1066142B (en) 1975-09-12 1976-08-18 Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.
CH1141676A CH614928A5 (en) 1975-09-12 1976-09-08
CA260,800A CA1066304A (en) 1975-09-12 1976-09-08 Process for manufacturing n-acyl derivatives of hydroxyarylgycines and novel products resulting therefrom
NL7609939A NL7609939A (en) 1975-09-12 1976-09-08 PROCESS FOR THE PREPARATION OF N-ACYLHYDROXYARYL GLYCINS.
DE19762640615 DE2640615A1 (en) 1975-09-12 1976-09-09 PROCESS FOR THE PREPARATION OF N-ACYLATED HYDROXYARYLGLYCINE DERIVATIVES AND THE PRODUCTS OBTAINED THEREOF
JP51108725A JPS5236644A (en) 1975-09-12 1976-09-09 Production of nnacyl derivatives of hydroxy arylglycine
GB37651/76A GB1520824A (en) 1975-09-12 1976-09-10 Process for manufacturing n-acyl derivatives of hydroxy-arylglycines
US05/722,284 US4105690A (en) 1975-09-12 1976-09-10 Process for manufacturing N-acyl derivatives of hydroxy-arylglycines
SE7610065A SE7610065L (en) 1975-09-12 1976-09-10 METHOD OF PREPARATION N-ACYLATED DERIVATIVES OF GLYCINS SUBSTITUTED WITH AROMATIC RADICALS
SE7610064A SE7610064L (en) 1975-09-12 1976-09-10 METHOD OF PREPARATION OF N-ACYLATED DERIVATIVES OF HYDROXYARYLGLYCINES

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7528151A FR2323680A1 (en) 1975-09-12 1975-09-12 Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.

Publications (2)

Publication Number Publication Date
FR2323680A1 true FR2323680A1 (en) 1977-04-08
FR2323680B1 FR2323680B1 (en) 1978-10-20

Family

ID=9159959

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7528151A Granted FR2323680A1 (en) 1975-09-12 1975-09-12 Alpha aromatic N-acyl glycine intermediates for penicillins - prepd. from an amido glycollic acid and an aromatic cpd.

Country Status (1)

Country Link
FR (1) FR2323680A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998017639A1 (en) * 1996-10-17 1998-04-30 Smithkline Beecham Plc Beta-thiopropionyl-amino acid derivatives and their use as beta-lactamase inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. CHEM. SOC. CHEM. COMM. 1975, PAGES 349-50 PUBLIE LE 7 MAI 1975 ) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998017639A1 (en) * 1996-10-17 1998-04-30 Smithkline Beecham Plc Beta-thiopropionyl-amino acid derivatives and their use as beta-lactamase inhibitors
US6156774A (en) * 1996-10-17 2000-12-05 Smithkline Beecham P.L.C. Beta-thiopropionyl-amino acid derivatives and their use as beta-lactamase inhibitors

Also Published As

Publication number Publication date
FR2323680B1 (en) 1978-10-20

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