Chloroacetic Acid → HCID 54366311, compound

Participants

Reaction Steps

To a solution of O-(2-amino-3-hydroxy-4,4,4-trifluoro-1-oxobutyl)-N-trifluoroacetyl-L-serine (685 mg) and chloroacetic acid (0.04 ml) in water (7 ml) was added sodium nitrite (227 mg) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was neutrized with 2M tris buffer solution to pH 7.0 to 7.3 and then Acylase I (acylase, Sigma A-7264, made by Sigma Chemicals) (140 mg) was added. The mixture was stirred for 6 hours at room temperature and chromatographed on carbon (60 ml) eluting successively with water and a 9:1 mixture of water and acetone to give a crude product, which was chromatographed on preparative thin layer chromatography eluting with a 65:35:4 mixture of chloroform, methanol and water, and lyophilized to give O-(2-diazo-3-hydroxy-4,4,4-trifluoro-1-oxobutyl)-L-serine (113 mg).

Provenance & Evidence