GB1339101A - Production of phenylalanine derivatives - Google Patents

Production of phenylalanine derivatives

Info

Publication number
GB1339101A
GB1339101A GB375972A GB1339101DA GB1339101A GB 1339101 A GB1339101 A GB 1339101A GB 375972 A GB375972 A GB 375972A GB 1339101D A GB1339101D A GB 1339101DA GB 1339101 A GB1339101 A GB 1339101A
Authority
GB
United Kingdom
Prior art keywords
phenylalanine
aspartyl
alkyl esters
protected
tertiary
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
GB375972A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB1339101A publication Critical patent/GB1339101A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Peptides Or Proteins (AREA)

Abstract

1339101 α-L-Aspartyl-L-phenylalanine alkyl esters G D SEARLE & CO 26 Jan 1972 3759/72 Heading C2C α-L-Aspartyl-L-phenylalanine C 1-4 alkyl esters of the formula in which R is C 1-4 alkyl are obtained by reacting N-protected-L-aspartic anhydrides, in which the N atoms are protected by tertiary-butoxy carbonyl or tertiary-amyloxycarbonyl groups, with C 1-4 alkyl esters of phenylalanine in inert organic solvents to form mixtures of N-protected- α-L-aspartyl-L-phenylalanine C 1-4 alkyl esters and N-protected-#-L-aspartyl-L-phenylalanine C 1-4 alkyl esters: and thereafter either (a) separating all or substantially all of the N-protected-#-L-aspartyl-L-phenylalanine C 1-4 alkyl esters from the N-protected-α-L-aspartyl-L- phenylalanine C 1-4 alkyl esters and eliminating the N-protecting groups from the N-protected-α- L-aspartyl-L-phenylalanine C 1-4 alkyl esters, or (b) eliminating the N-protecting groups from the mixtures of N-protected-α- and #-aspartyl-L- phenylalanine C 1-4 alkyl esters and separating all or substantially all of the #-L-aspartyl-L- phenylalanine C 1-4 alkyl esters from the α-L- aspartyl-L-phenylalanine C 1-4 alkyl esters. N-Tertiary-butoxycarbonyl-L-aspartic anhydride and N-tertiary-amyloxycarbonyl-L-aspartic anhydride are obtained by reacting N-tertiarybutoxy-carbonylaspartic acid and N-tertiaryamyloxy-carbonylaspartic acid respectively with acetic anhydride.
GB375972A 1972-01-26 1972-01-26 Production of phenylalanine derivatives Expired GB1339101A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB375972 1972-01-26

Publications (1)

Publication Number Publication Date
GB1339101A true GB1339101A (en) 1973-11-28

Family

ID=9764429

Family Applications (1)

Application Number Title Priority Date Filing Date
GB375972A Expired GB1339101A (en) 1972-01-26 1972-01-26 Production of phenylalanine derivatives

Country Status (1)

Country Link
GB (1) GB1339101A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2153365A (en) * 1984-01-26 1985-08-21 Pierrel Spa Process for the preparation of N-acyl-derivatives of aspartame
EP0214550A2 (en) * 1985-09-09 1987-03-18 Hoechst Aktiengesellschaft Process for the preparation of aspartame and agent for its preparation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2153365A (en) * 1984-01-26 1985-08-21 Pierrel Spa Process for the preparation of N-acyl-derivatives of aspartame
EP0214550A2 (en) * 1985-09-09 1987-03-18 Hoechst Aktiengesellschaft Process for the preparation of aspartame and agent for its preparation
EP0214550A3 (en) * 1985-09-09 1988-08-10 Hoechst Aktiengesellschaft Process for the preparation of aspartame and agent for its preparation

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years