Acetic Anhydride → (2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

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Reaction Steps

2.66 g (10 millimole) of N-carbobenzoxy-L-asparagine (Journal of Organic Chemistry, 26, 3356-3360 (1961)) was admixed with 30 ml of dry pyridine and 1.2 ml (12 millimole) of acetic anhydride, and the admixture obtained was stirred at a temperature from 20° to 25° C. for one hour. The reaction solution was then concentrated to a syrup by distilling off pyridine under reduced pressure, and the residue was diluted with 50 ml of 1 N hydrochloric acid. The product deposited as colorless needles was collected by filtration, washed with cold water and dried to afford 2.05 g of N-carbobenzoxy-β-cyano-L-alanine. Yield 83%. This product was found to have the following properties:

Provenance & Evidence