GB867572A - Hydroxyl-and mercapto-alkanoyl-amino-carboxylic acid amides and process for their manufacture - Google Patents

Hydroxyl-and mercapto-alkanoyl-amino-carboxylic acid amides and process for their manufacture

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Publication number
GB867572A
GB867572A GB30749/57A GB3074957A GB867572A GB 867572 A GB867572 A GB 867572A GB 30749/57 A GB30749/57 A GB 30749/57A GB 3074957 A GB3074957 A GB 3074957A GB 867572 A GB867572 A GB 867572A
Authority
GB
United Kingdom
Prior art keywords
benzoyl
glycyl
amide
seryl
hydroxy
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
GB30749/57A
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 GB867572A publication Critical patent/GB867572A/en
Expired legal-status Critical Current

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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
    • C07C323/60—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 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • 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
    • C07C323/52—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 acyclic and saturated
    • 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

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

Abstract

Hydroxy- and mercapto-alkanoyl-aminocarboxylic acid amides of the formula: <FORM:0867572/IV (b)/1> wherein X represents oxygen or sulphur, R the divalent radical of an a -amino-carboxylic acid after the deduction of the amino and carboxylic groups and R1 represents hydrogen or the radical of an amino acid or peptide, are produced by the action of a hydrocarbon compound of an alkali or alkaline earth metal or an amide or tertiary alcoholate of such a metal, on an ester of the formula: <FORM:0867572/IV (b)/2> By esterification of the hydroxyl or mercapto group (see first formula) with an a -amino acid followed by repetition of the molecular rearrangement, the peptide can be lengthened by any number of the same or different amino acid radicals. Sodamide, potassium tertiary butylate, sodium phenyl or lithium phenyl may be used to effect the molecular rearrangement. The metal amides are preferably used in the presence of liquid ammonia; while the metallic alcoholates are employed in the corresponding alcohol. In Example 1, carbobenzoxy glycine anhydride is reacted with b -hydroxy-b -methyl propionic acid amide to give o-(carbobenzoxy-glycyl)b -hydroxy-b -methyl-propionic acid amide, which is then treated with hydrogen in the presence of hydrochloric acid and palladium charcoal to obtain o-glycyl-b -hydroxy-b methyl propionic acid amide hydrochloride. Molecular rearrangement of the latter, by means of potassium tertiary butylate in tertiary butanol, yields b -hydroxy-b -methyl propionyl-glycinamide. In Example 2, Nbenzoyl-serine is esterified with diazomethane and the ester is treated with a methanolic solution of ammonia to give N-benzoyl serinamide. The latter is reacted with carbobenzoxy glycine anhydride and the product is reduced with hydrogen in the presence of hydrochloric acid and palladium-charcoal to give o-glycyl-N-benzoyl-serinamide hydrochloride. Molecular rearrangement of the latter compound, by means of sodium dissolved in liquid ammonia, yields Nbenzoyl-seryl-glycinamide. Example 3 describes the preparation of o-glycyl-N-(benzoyl-glycyl)DL-serinamide hydrochloride, and its conversion into N-(benzoyl-glycyl)-DL-serylglycinamide. Example 4 describes the preparation of o-glycyl-N-benzoyl-L-serinamide hydrochloride, and its conversion into Nbenzoyl-L-seryl-glycinamide. Example 5 describes the preparation of o-glycyl-N-benzoyl-DL-threoninamide perchlorate, and its conversion into N-benzoyl-DL-threonylglycinamide. Example 6 indicates the preparation of o-(carboxy-L-phenylalanyl)-N-benzoylL-seryl-glycine amide and its conversion into N- benzoyl- L- seryl- L- phenylalanylglycineamide. In Example 7, N-benzoyl-L-serinamide is treated with thionyl chloride followed by sodium carbonate to yield 2-phenyl-4-carbamino-oxazoline. The oxazoline is reacted with N-carbobenzoxy thioglycine to give s-(carbobenzoxy glycyl-N-benzoyl-L-cysteinamide, which is then treated with phosphonium iodide in glacial acetic acid to obtain s-glycyl-N-benzoyl-L-cystein-amide, and this is then treated with potassium tertiary butylate followed by benzyl alcohol to yield S-benzylN-benzoyl-L-cysteinyl-glycine amide. In Example 8, leucine isopropyl ester is agitated with potassium carbonate and potassium tertiary butylate in tertiary butanol. Seryl-leucine amide is formed, but undergoes further esterification and rearrangement whereby a serylpolyleucine amide is produced. Specification 831,973 is referred to.
GB30749/57A 1956-10-17 1957-10-01 Hydroxyl-and mercapto-alkanoyl-amino-carboxylic acid amides and process for their manufacture Expired GB867572A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH867572X 1956-10-17

Publications (1)

Publication Number Publication Date
GB867572A true GB867572A (en) 1961-05-10

Family

ID=4543777

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30749/57A Expired GB867572A (en) 1956-10-17 1957-10-01 Hydroxyl-and mercapto-alkanoyl-amino-carboxylic acid amides and process for their manufacture

Country Status (1)

Country Link
GB (1) GB867572A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1144360A1 (en) * 1999-01-22 2001-10-17 Transtech Pharma, Inc. A method for the synthesis of compounds of formula 1 and derivatives thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1144360A1 (en) * 1999-01-22 2001-10-17 Transtech Pharma, Inc. A method for the synthesis of compounds of formula 1 and derivatives thereof
EP1144360A4 (en) * 1999-01-22 2003-02-19 Pharmacore Inc A method for the synthesis of compounds of formula 1 and derivatives thereof
US6930200B2 (en) 1999-01-22 2005-08-16 Pharmacore, Inc. Multicomponent synthesis of amino acids and derivatives thereof

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