Synthesis 2005(15): 2578-2582  
DOI: 10.1055/s-2005-872101
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one and Some N-Acyl Derivatives from (R)-Phenylglycine

Alessandro Rodrigues*a, Paulo Roberto Olivato*a, Roberto Rittnerb
a Conformational Analysis and Electronic Interactions Laboratory, Instituto de Química, Universidade de São Paulo, C.P. 26077, São Paulo, SP 05513-970, Brazil
Fax: +55(11)38155579; e-Mail: alessand@iq.usp.br; e-Mail: prolivat@iq.usp.br;
b Physical Organic Chemistry Laboratory, Chemistry Institute, State University of Campinas, C.P. 6154, Campinas, SP 13084-971, Brazil
Further Information

Publication History

Received 30 March 2005
Publication Date:
25 July 2005 (eFirst)

Abstract

(5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one was synthesized from (R)-phenylglycine in five steps and in 65% overall yield. In addition, a convenient and practical method for N-acyl­ation of 1,3,4-oxadiazinan-2-one directly with acids in the presence of DCC and catalytic quantities of DMAP is described. The acyl­ated products were obtained in excellent yields.

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This product was used without further purification, is quite sensitive, and had to be stored at -20 °C to avoid decomposition.