ACYLAMINATION BY MEANS OF N-BENZYLOXYCARBONYLCARBOXAMIDES
- 5 August 1973
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 2 (8) , 821-824
- https://doi.org/10.1246/cl.1973.821
Abstract
The reaction of N-benzyloxycarbonylcarboxamides with alkyl sulfonates or halides gave N-alkylated and O-alkylated products. On treatment with HBr-AcOH, the N-alkyl-N-benzyloxycarbonylcarboxamides were converted to N-alkylcarboxamides. When N-benzyloxycarbonylbenzamide was allowed to react with (S)-(−)-ethyl lactate, triphenylphosphine and diethyl azodicarboxylate, followed by treatment with HBr-AcOH, (R)-(−)-N-benzoylalanine ethyl ester was obtained with high optical purity.Keywords
This publication has 1 reference indexed in Scilit:
- Stereospecific and stereoselective reactions. I. Preparation of amines from alcoholsJournal of the American Chemical Society, 1972