FR2446273A1 - N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride - Google Patents

N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride

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Publication number
FR2446273A1
FR2446273A1 FR7900615A FR7900615A FR2446273A1 FR 2446273 A1 FR2446273 A1 FR 2446273A1 FR 7900615 A FR7900615 A FR 7900615A FR 7900615 A FR7900615 A FR 7900615A FR 2446273 A1 FR2446273 A1 FR 2446273A1
Authority
FR
France
Prior art keywords
glycine
reaction
acid
condensn
prepd
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
FR7900615A
Other languages
French (fr)
Other versions
FR2446273B1 (en
Inventor
Alain Schouteeten
Yani Christidis
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.)
Sanofi Aventis France
Original Assignee
Francaise Hoechst Ste
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 Francaise Hoechst Ste filed Critical Francaise Hoechst Ste
Priority to FR7900615A priority Critical patent/FR2446273A1/en
Publication of FR2446273A1 publication Critical patent/FR2446273A1/en
Application granted granted Critical
Publication of FR2446273B1 publication Critical patent/FR2446273B1/fr
Granted legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Racemic N-methoxycarbonyl 2-(p-hydroxyphenyl)-glycine (I), is new. Used for the prepn. of DL-2-(p-hydroxyphenyl)-glycine (II) by alkaline hydrolysis of (I). (II) is an intermediate used to prepare semi-synthetic penicillins etc. (I) is prepd. by condensn. of glyoxylic acid with excess (=25%) methyl carbamate in acetic acid at room temp. and then reaction of this prod. in the same medium without isolation, with excess (10-500%) phenol and an equimolecular quantity of hydrogen chloride. The reaction mixt. is concn. to half its vol. and treated with chloroform to produce a suspension which is filtered to isolate (I). A further crop of (I) may be obtd. by heating the mother liquors at reflux with azeotropic distillation of water, in the presence of a strong acid (pref. p-toluene sulphonic acid), and filtration of the obtd. suspension.
FR7900615A 1979-01-11 1979-01-11 N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride Granted FR2446273A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7900615A FR2446273A1 (en) 1979-01-11 1979-01-11 N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7900615A FR2446273A1 (en) 1979-01-11 1979-01-11 N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride

Publications (2)

Publication Number Publication Date
FR2446273A1 true FR2446273A1 (en) 1980-08-08
FR2446273B1 FR2446273B1 (en) 1982-07-09

Family

ID=9220628

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7900615A Granted FR2446273A1 (en) 1979-01-11 1979-01-11 N-methoxy-carbonyl 2-para-hydroxy-phenyl-glycine - prepd. by condensn. of glyoxylic acid and methyl carbamate in acetic acid and reaction of prod. with phenol and hydrogen chloride

Country Status (1)

Country Link
FR (1) FR2446273A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2769310A1 (en) * 1997-10-08 1999-04-09 Rhodia Chimie Sa A new process for the amidoalkylation of a phenolic compound substituted with an electron donor group

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2253738A1 (en) * 1973-12-06 1975-07-04 Smithkline Corp

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2253738A1 (en) * 1973-12-06 1975-07-04 Smithkline Corp

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2769310A1 (en) * 1997-10-08 1999-04-09 Rhodia Chimie Sa A new process for the amidoalkylation of a phenolic compound substituted with an electron donor group
WO1999018064A1 (en) * 1997-10-08 1999-04-15 Rhodia Chimie Method for functionalizing a phenolic compound bearing an electron-donor group
CN100366604C (en) * 1997-10-08 2008-02-06 罗狄亚化学公司 Method for functionalizing phenolic compound bearing electron-donor group

Also Published As

Publication number Publication date
FR2446273B1 (en) 1982-07-09

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