Preparation of an electrophilic glycine cation equivalent and its reaction with heteroatom nucleophiles

MJ O'Donnell, WD Bennett, RL Polt

Index: O'Donnell, Martin J.; Bennett, William D.; Polt, Robin L. Tetrahedron Letters, 1985 , vol. 26, # 6 p. 695 - 698

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Citation Number: 29

Abstract

Preparation of ethyl-N-(diphenylmethylene)-2-acetoxyglycinate: a solution of N-bromosuccinimide (13.9 g, 78 mmol) dissolved in dry DMF (40 ml) was added dropwise at room temperature with stirring over three hours to a mixture of Schiff base 3 (16.05 g, 60 mmol), anhydrous sodium acetate (16.5 g, 201 mmol) and N,N-dimethylformamide (60 ml, distilled from calcium hydride) in a 500 ml round-bottom flask equipped with a magnetic stirrerand a dropping funnel (CaCl 2 ...