GB1078445A - Process for the preparation of l-(-)-ª‡-methyl-ª‰-(3,4-dihydroxy-phenyl)-alanine - Google Patents

Process for the preparation of l-(-)-ª‡-methyl-ª‰-(3,4-dihydroxy-phenyl)-alanine

Info

Publication number
GB1078445A
GB1078445A GB2760766A GB2760766A GB1078445A GB 1078445 A GB1078445 A GB 1078445A GB 2760766 A GB2760766 A GB 2760766A GB 2760766 A GB2760766 A GB 2760766A GB 1078445 A GB1078445 A GB 1078445A
Authority
GB
United Kingdom
Prior art keywords
methyl
dimethoxyphenyl
alanine
sulphonic acid
alaninamide
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
GB2760766A
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.)
Roche Diagnostics GmbH
CF Boehringer und Soehne GmbH
Original Assignee
Boehringer Mannheim GmbH
CF Boehringer und Soehne GmbH
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 Boehringer Mannheim GmbH, CF Boehringer und Soehne GmbH filed Critical Boehringer Mannheim GmbH
Publication of GB1078445A publication Critical patent/GB1078445A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles

Landscapes

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

Abstract

L - (-) - a - Methyl - b - (3,4 - dihydroxyphenyl)-alanine is prepared by reacting 3,4-dimethoxyphenyl-acetone or a bisulphite adduct thereof with an alkali metal cyanide and D-(-)-a -methylbenzylamine to give L-(-)-threo - a - (3,4 - dimethoxybenzyl) - a - (N - a -methylbenzylamino)-propionitrile which is partially hydrolysed with concentrated sulphuric acid to give L-(-)-threo-a -methyl-b -(3,4-dimethoxyphenyl - 6 - sulphonic acid) - a - (N - a - methylbenzyl) -alaninamide, followed, in any desired order, by removal of the a -methylbenzyl radical by catalytic hydrogenation, demethylation by hydrolysis, removal of the sulphonic acid group by hydrolysis, and conversion of the amide group into a free carboxylic acid group by hydrolysis. The L - (-) - threo - a - methyl - b - (3,4 - dimethoxyphenyl - 6 - sulphonic acid) - a - (N - a - methylbenzyl) -alaninamide may be converted into L - (-) - a - methyl - b - (3,4 - dimethoxyphenyl - 6 - sulphonic acid) - alaninamide by catalytic hydrogenation. This compound is then converted to L-(-)-a -methyl-b -(3,4-dihydroxyphenyl) -alanine.
GB2760766A 1965-06-23 1966-06-21 Process for the preparation of l-(-)-ª‡-methyl-ª‰-(3,4-dihydroxy-phenyl)-alanine Expired GB1078445A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0082530 1965-06-23

Publications (1)

Publication Number Publication Date
GB1078445A true GB1078445A (en) 1967-08-09

Family

ID=6981537

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2760766A Expired GB1078445A (en) 1965-06-23 1966-06-21 Process for the preparation of l-(-)-ª‡-methyl-ª‰-(3,4-dihydroxy-phenyl)-alanine

Country Status (12)

Country Link
AT (1) AT266094B (en)
BE (1) BE682958A (en)
CH (1) CH490334A (en)
DE (1) DE1493484C3 (en)
DK (1) DK111449C (en)
ES (1) ES328220A2 (en)
FI (1) FI44006C (en)
FR (1) FR91409E (en)
GB (1) GB1078445A (en)
LU (1) LU51385A1 (en)
NL (1) NL6608715A (en)
SE (1) SE345444B (en)

Also Published As

Publication number Publication date
FI44006C (en) 1971-08-10
DK111449B (en) 1968-08-26
AT266094B (en) 1968-11-11
DK111449C (en) 1981-11-02
FR91409E (en) 1968-11-08
ES328220A2 (en) 1967-04-01
CH490334A (en) 1970-05-15
NL6608715A (en) 1966-12-27
LU51385A1 (en) 1966-08-22
SE345444B (en) 1972-05-29
DE1493484A1 (en) 1969-04-17
FI44006B (en) 1971-04-30
BE682958A (en) 1966-12-22
DE1493484C3 (en) 1974-01-24
DE1493484B2 (en) 1973-06-14

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