GB1069776A - Process for the preparation of 3-(3',4'-dihydroxyphenyl)-2-methyl alanine and of its derivatives - Google Patents

Process for the preparation of 3-(3',4'-dihydroxyphenyl)-2-methyl alanine and of its derivatives

Info

Publication number
GB1069776A
GB1069776A GB2454964A GB2454964A GB1069776A GB 1069776 A GB1069776 A GB 1069776A GB 2454964 A GB2454964 A GB 2454964A GB 2454964 A GB2454964 A GB 2454964A GB 1069776 A GB1069776 A GB 1069776A
Authority
GB
United Kingdom
Prior art keywords
dihydroxyphenyl
methylalanine
dimethoxyphenyl
chloro
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
Application number
GB2454964A
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.)
Egyesult Gyogyszer es Tapszergyar
Egyt Gyogyszervegyeszeti Gyar
Original Assignee
Egyesult Gyogyszer es Tapszergyar
Egyt Gyogyszervegyeszeti Gyar
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 Egyesult Gyogyszer es Tapszergyar, Egyt Gyogyszervegyeszeti Gyar filed Critical Egyesult Gyogyszer es Tapszergyar
Publication of GB1069776A publication Critical patent/GB1069776A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (a) methyl 3-(31,41 -dimethoxyphenyl) - 2 - chloro - 2 - methylpropionate and 3 - (31,41 - dimethoxyphenyl) - 2 - chloro - 2 - methylpropionic acid, and (b) the preparation of 3,(31,41-dihydroxyphenyl)-2 -methylalanine and its acyl derivatives by reacting diazotized 4-aminoveratrole in the presence of cupric chloride in an aqueous or aqueous-organic medium with methyl methacrylate hydrolysing the resulting methyl 3-(31,41 - dimethoxyphenyl) - 2 - chloro - 2 - methyl-propionate and aminating the 3-(31,41-dimethoxyphenyl) - 2 - chloro - 2 - methylpropionic acid obtained to yield 3-(31,41dimethoxyphenyl)-2 -methylalanine, which may then be demethylated to give 3-(31,41-dihydroxyphenyl)-2-methylalanine or, alternatively, may first be N-acylated and the N-acyl-dimethoxy compound then demethylated, and the resulting N-acyldihydroxy compound be acylated to the N,O,O-triacyl derivative. The N,O,O-triazyl derivative may then be deacylated to yield 3-(31,41 -dihydroxyphenyl) - 2 - methylalanine. 3-(31,41-dihydroxyphenyl) -2-methylalanine prepared by these methods is converted, if desired, into an acid addition salt.
GB2454964A 1963-06-13 1964-06-12 Process for the preparation of 3-(3',4'-dihydroxyphenyl)-2-methyl alanine and of its derivatives Expired GB1069776A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUEE001022 1963-06-13

Publications (1)

Publication Number Publication Date
GB1069776A true GB1069776A (en) 1967-05-24

Family

ID=10995156

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2454964A Expired GB1069776A (en) 1963-06-13 1964-06-12 Process for the preparation of 3-(3',4'-dihydroxyphenyl)-2-methyl alanine and of its derivatives

Country Status (4)

Country Link
AT (1) AT248422B (en)
DK (1) DK111361B (en)
GB (1) GB1069776A (en)
NL (2) NL6406706A (en)

Also Published As

Publication number Publication date
NL125246C (en)
NL6406706A (en) 1964-12-14
AT248422B (en) 1966-07-25
DE1493619A1 (en) 1969-06-12
DK111361B (en) 1968-08-05

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