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

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.

Key words

(R)-phenylglycine - 1,3,4-oxadiazinan-2-ones - heterocycles - acylation - carboxylic acids

References

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8

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