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- Title
Synthesis of phosphinic acids on the basis of hypophosphites: VI. General methods for synthesis of pseudo-γ-glutamylpeptides.
- Authors
Ragulin, V. V.
- Abstract
A general method for synthesis of 2-substituted pseudo-γ-glutamylpeptides, namely, [2-(hydroxycarbonyl)ethyl][3-amino-3-(hydroxycarbonyl)propyl]phosphinic acids I which are phosphinic acid analogs of γ-glutamylpeptides. Bis(trimethylsilyl) hypophosphite ( IV) formed from ammonium hypophosphite ( II) in situ was added to the respective α-substituted acrylate to form bis(trimethylsilyl) [2-R-2-(alkoxycarbonyl)ethyl]-phosphonites V. Treatment of compounds V in situ with excess dibromoethane followed by alcoholysis gave [2-R-2-(alkoxycarbonyl)ethyl](2-bromoethyl)phosphinic acids VI which without isolation were treated with excess triethyl orthoformate. The simultanious esterification and dehydrobromination led to [2-R-2-(alkoxy-carbonyl)ethyl](vinyl)phosphinates III which were isolated and characterized. The Michael addition of diethyl acetamidomalonate to vinylphosphinates III followed by acid hydrolysis of phosphinates VII without their isolation resulted in formation of target [2-R-2-(hydroxycarbonyl)ethyl][3-amino-3-(hydroxycarbonyl)]proly]phosphinic acids-pseudo-γ-glutamylpeptides I.
- Subjects
HYPOPHOSPHITES; MATERIA medica; ETHYLENE dibromide; ETHANES; AMINO acid synthesis; CHEMISTRY
- Publication
Russian Journal of General Chemistry, 2007, Vol 77, Issue 5, p861
- ISSN
1070-3632
- Publication type
Article
- DOI
10.1134/S1070363207050076