Synthesis of amino acid diazoketones

George Pettit, Paul S. Nelson

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt-Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide-tetrahydrofuran followed by diazomethane at -23°C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23-26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

Original languageEnglish (US)
Pages (from-to)2097-2102
Number of pages6
JournalCanadian Journal of Chemistry
Volume64
Issue number11
StatePublished - 1986

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Diazomethane
Amino acids
Esters
Carboxylic Acids
Carboxylic acids
Amino Acids
Chlorides
Dimethylformamide
Carbon Dioxide
Glutamic Acid
Substitution reactions
Acids
Temperature
oxalyl chloride
tetrahydrofuran

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Catalysis

Cite this

Synthesis of amino acid diazoketones. / Pettit, George; Nelson, Paul S.

In: Canadian Journal of Chemistry, Vol. 64, No. 11, 1986, p. 2097-2102.

Research output: Contribution to journalArticle

Pettit, G & Nelson, PS 1986, 'Synthesis of amino acid diazoketones', Canadian Journal of Chemistry, vol. 64, no. 11, pp. 2097-2102.
Pettit, George ; Nelson, Paul S. / Synthesis of amino acid diazoketones. In: Canadian Journal of Chemistry. 1986 ; Vol. 64, No. 11. pp. 2097-2102.
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