GB625949A - Synthesis of ª‡-acylamido-ª‰, ª‰-dimethylacrylic acids and esters thereof - Google Patents

Synthesis of ª‡-acylamido-ª‰, ª‰-dimethylacrylic acids and esters thereof

Info

Publication number
GB625949A
GB625949A GB6687/47A GB668747A GB625949A GB 625949 A GB625949 A GB 625949A GB 6687/47 A GB6687/47 A GB 6687/47A GB 668747 A GB668747 A GB 668747A GB 625949 A GB625949 A GB 625949A
Authority
GB
United Kingdom
Prior art keywords
acid
dimethylacrylic
acylamido
esters
amino
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
GB6687/47A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB625949A publication Critical patent/GB625949A/en
Expired legal-status Critical Current

Links

Abstract

a -Acylamido-b : b -dimethylacrylic acids and esters thereof are manufactured by treating a - amino - b - methoxyisovaleric acid with an aqueous solution of an alkali metal salt of an aliphatic carboxylic acid (e.g. sodium acetate or potassium propionate) and an aliphatic carboxylic acid anhydride (e.g. acetic or propionic anhydride), and, if desired, reacting the product with an aliphatic alcohol, containing up to 4 carbon atoms in the molecule, in the presence of a mineral acid catalyst (e.g. hydrogen bromide or chloride). The esters yield dl-penicillamine on treatment with hydrogen sulphide, preferably in the presence of an alkali or alkaline - earth metal alcoholate. Examples describe the preparation of a -acetyl-amino-b : b -dimethylacrylic acid and its methyl (or ethyl, propyl, isopropyl or butyl) ester. a -Amino-b -methoxyisovaleric acid is obtainable by reacting dimethylacrylic acid with mercuric acetate in methanol to produce a compound of the formula <FORM:0625949/IV (b)/1> which is brominated in aqueous potassium bromide solution to form a -bromo-b -methoxyisovaleric acid and the bromine atom is replaced by an amino group by the action of aqueous ammonium hydroxide. The Specification as open to inspection under Sect. 91 comprises also a reference to aralkyl esters of the a -acylamido-b : b -dimethylacrylic acids and to products in which the acylamido group contains an aryl or aralkyl radical. This subject-matter does not appear in the Specification as accepted.
GB6687/47A 1946-03-22 1947-03-10 Synthesis of ª‡-acylamido-ª‰, ª‰-dimethylacrylic acids and esters thereof Expired GB625949A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US625949XA 1946-03-22 1946-03-22

Publications (1)

Publication Number Publication Date
GB625949A true GB625949A (en) 1949-07-06

Family

ID=22043510

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6687/47A Expired GB625949A (en) 1946-03-22 1947-03-10 Synthesis of ª‡-acylamido-ª‰, ª‰-dimethylacrylic acids and esters thereof

Country Status (1)

Country Link
GB (1) GB625949A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2217706A (en) * 1988-07-07 1989-11-01 W A Gibbons alpha -Amino-alkanoic acid derivatives and process for their preparation with anti-inflammatory, analgesic, sedative, hypnotic, anxiolytic, spasmolytic, anaesthetic, muscle relaxant and cardiovascular activity
WO1996016021A1 (en) * 1994-11-17 1996-05-30 E.I. Du Pont De Nemours And Company Process for the efficient preparation of n-substituted dehydroamino acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2217706A (en) * 1988-07-07 1989-11-01 W A Gibbons alpha -Amino-alkanoic acid derivatives and process for their preparation with anti-inflammatory, analgesic, sedative, hypnotic, anxiolytic, spasmolytic, anaesthetic, muscle relaxant and cardiovascular activity
WO1996016021A1 (en) * 1994-11-17 1996-05-30 E.I. Du Pont De Nemours And Company Process for the efficient preparation of n-substituted dehydroamino acid esters

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