GB777207A - A process for the manufacture of acid hydrazides of acylated -a-amino acids - Google Patents

A process for the manufacture of acid hydrazides of acylated -a-amino acids

Info

Publication number
GB777207A
GB777207A GB34520/55A GB3452055A GB777207A GB 777207 A GB777207 A GB 777207A GB 34520/55 A GB34520/55 A GB 34520/55A GB 3452055 A GB3452055 A GB 3452055A GB 777207 A GB777207 A GB 777207A
Authority
GB
United Kingdom
Prior art keywords
acid
ester
acetyl
acylated
thiophenyl
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
GB34520/55A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB777207A publication Critical patent/GB777207A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof

Landscapes

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

Abstract

Isonicotinic and 2-methylisonicotinic acid hydrazides of acylated a -amino acids of the general formula <FORM:0777207/IV(b)/1> wherein R1-CO- is an N-acylated acyl group of an a -aminoacid and R2 is hydrogen or methyl, are made by reacting a thiol (e.g. thiophenol or thioglycolic acid) ester of an acylated a -amino acid with isonicotinic acid hydrazide or 2-methylisonicotinic acid hydrazide preferably in a solvent such as ethyl acetate, glacial acetic acid, pyridine, aqueous sodium bicarbonate solution or alcoholic sodium ethoxide, and preferably at the boiling temperature of the solvent. Examples describe the reaction of isonicotinic acid hydrazide with dl acetylmethionine thiophenyl ester; dl acetyl-methionine thioglycolic ester; aceturic acid thiophenyl ester and dl acetyl-b -phenylalanine thiophenyl ester, and of 2-methyl-isonicotinic acid hydrazide with dl acetyl-methionine thiophenyl ester to give the corresponding N-(acylaminoacyl)-N1-isonicotinyl-hydrazine compounds. Starting materials. The thiol esters which are used as starting materials are made by reacting an acylated a -amino acid, such as acetylmethionine, with an acid chloride (e.g. isovaleric acid chloride) to give a mixed anhydride, which is reacted with the thiol compound (e.g. thiophenol or thioglycolic acid) to give the appropriate thiol ester such as the thiophenyl esters of dl acetyl-methionine, aceturic acid and dl-acetyl-b -phenyl-alanine and the thioglycolic acid ester of dl-acetyl-methionine. Specification 735,685 is referred to.
GB34520/55A 1954-12-03 1955-12-02 A process for the manufacture of acid hydrazides of acylated -a-amino acids Expired GB777207A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH777207X 1954-12-03

Publications (1)

Publication Number Publication Date
GB777207A true GB777207A (en) 1957-06-19

Family

ID=4535908

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34520/55A Expired GB777207A (en) 1954-12-03 1955-12-02 A process for the manufacture of acid hydrazides of acylated -a-amino acids

Country Status (1)

Country Link
GB (1) GB777207A (en)

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