Preparation of (2-Methyl-propane-2-sulfonylimino) Acetic Acid Ethyl Ester

Abstract

Synthesis of (2-methyl-propane-2-sulfonylimino) acetic acid ethyl ester from tert-butylsulfonamide, thionyl chloride and ethyl glyoxylate is described. The N-tert-butylsulfonyl imino ester has served as a substitute of the corresponding N-toluenesulfonyl imino ester in allylation reactions.

imino ester - allylation - amino acids

References

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A technical 50% solution of ethyl glyoxylate in toluene was concentrated at atmospheric pressure and the residue was distilled to give ethyl glyoxylate as a turbid yellow oil. A second distillation of this material at atmospheric pressure by using a 20 cm Vigreux column at a bath temperature of 160-180 °C furnished ethyl glyoxylate as a yellow fluid, which was used immediately and transferred to the reaction mixture by a syringe.