GB783959A - Process for the manufacture of aminoacyl compounds - Google Patents

Process for the manufacture of aminoacyl compounds

Info

Publication number
GB783959A
GB783959A GB31621/53A GB3162153A GB783959A GB 783959 A GB783959 A GB 783959A GB 31621/53 A GB31621/53 A GB 31621/53A GB 3162153 A GB3162153 A GB 3162153A GB 783959 A GB783959 A GB 783959A
Authority
GB
United Kingdom
Prior art keywords
acid
give
carbobenzyloxyaminoacetyl
aminoacetyl
glycine
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
GB31621/53A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB783959A publication Critical patent/GB783959A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton

Abstract

Aminoacyl derivatives of amines and alcohols are prepared by reacting an amine or alcohol with an S-aminoacylmercapto compound of formula A-X-CO-S-Y-Z wherein A is a substituted or unsubstituted amino group, X and Y are divalent organic radicals and Z is a carboxyl group or a salt thereof. The S-aminoacylmercapto compounds and their preparation are described in Specification 780,943. Amino and hydroxy compounds which may be reacted are aliphatic, alicyclic, aromatic, araliphatic or heterocyclic diamines or alcohols, in particular natural or synthetic aminocarboxylic acids, peptides or proteins. Specified compounds are serine, cystine, aminobutyric acids, valine, leucine, phenylalanine, tyrosine, tryptophane, histidine, lambda-carbobenzyloxy-ornithine, asparagine, asparaginic acid, glutaminic acid, proline, diglycine methionyl-glycine, and glutathione. Specified S-aminoacylmercapto compounds are S-(benzoylamino - acetyl) - b - mercaptopropionic acid, and S - (aminoacetyl) - or S - (phthalylamino - acetyl)- or S-[N-(N-carbobenzyloxyaminoacetyl - aminoacetyl) - aminoacetyl] - or S - [N - (N - aminoacetyl-aminoacetyl) - aminoacetyl] - mercaptoacetic acid. The process may be carried out with or without a solvent such as water, an alcohol, or dimethyl-formamide. In examples: (1) S-(benzoylamino-acetyl)-mercaptoacetic acid is reacted with aniline to give, benzoylaminoacetanilide, benzylamine to give benzoylaminoacetic acid benzylamide, aminoacetic acid to give benzoylaminoacetyl-aminoacetic acid and isonicotinic acid hydrazide to give N - benzoylaminoacetyl - N1 - isonicotinylhydrazine; (2) S-carbobenzyloxyamino-acetyl)-mercaptoacetic acid is reacted with aminoacetic acid to give carbobenzyloxyaminoacetyl-aminoacetic acid, glycyl-glycine to give carbobenzyloxy - diglycyl - glycine, dl - alanyl - glycine to give carbobenzyloxyaminoacetyl - dl - alanyl - glycine, dl - methionine to give carbobenzyloxyaminoacetyl - dl - methionine and ethylenediamine to give N:N1 - di - (carbobenzyloxyaminoacetyl) - ethylenediamine; (3) S - carbobenzyloxyaminoacetyl - thiosalicylic acid is reacted with aminoacetic acid to give carbobenzyloxaminoacetyl - aminoacetic acid and glycyl-glycine to give carbobenzyloxy-diglycylglycine; (4) S-(benzoylaminoacetyl)-thiosalicylic acid is reacted with aminoacetic acid to give benzoylaminoacetyl-aminoacetic acid.
GB31621/53A 1953-03-06 1953-11-13 Process for the manufacture of aminoacyl compounds Expired GB783959A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH783959X 1953-03-06

Publications (1)

Publication Number Publication Date
GB783959A true GB783959A (en) 1957-10-02

Family

ID=4536432

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31621/53A Expired GB783959A (en) 1953-03-06 1953-11-13 Process for the manufacture of aminoacyl compounds

Country Status (1)

Country Link
GB (1) GB783959A (en)

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