Hydrochloric Acid → HCID 178470518, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred, room temperature solution of ethyl cyanoformate (19.57 g, 0.1975 mol) in pyridine (78 mL) was added a chilled (+5° C.) mixture of trifluoroacetic acid (33 mL) and pyridine (118 mL) followed by sodium azide (14.06 g, 0.2163 mol), and the mixture was heated at 60° C. for 46 hours. The mixture was allowed to cool, poured into a mixture of concentrated hydrochloric acid (180 mL) and ice (400 g), and extracted with ethyl acetate several times. The extracts were washed with saturated sodium chloride, dried (MgSO4), and rotoevaporated to an oil. The oil was chromatographed on silica gel (500 g, 70-230 mesh) using ethyl acetatemethanol (15:1, 10×1 L) as eluent. Fractions containing product were rotoevaporated to an oil. The oil was dissolved in chloroform, filtered to remove a precipitate, and the filtrate extracted with aqueous sodium hydroxide. The extracts were acidified to pH 1 and extracted with ethyl acetate. The extracts were dried (MgSO4) and rotoevaporated to a white solid, yield 1.91 g (7%) of the title compound, mp=87.5°-91.5° C.

Provenance & Evidence