Sodium hydride → HCID 15035855, compound

Participants

Reaction Steps

(2-(t-Butyloxycarbonyl-amino)-ethyl)-(3-chloro-2-hydroxypropyl)-thioether (30 g, 111.52 mmole) from Example 3, was dissolved in dimethylformamide (500 mL) at 0° C. and treated with sodium hydride (9.81 g, 245 mmole) in 3 portions over 15 minutes. The reaction was allowed to warm to room temperature over 1 hour and 15 minutes, poured into 2.5 L ice water and extracted with 3×1 L chloroform. The combined organic extracts were dried with brine and Na2SO4, evaporated, and the resulting residue chromatographed (3:1 hexane:ethyl acetate, silica gel) to obtain the product as a white solid (12.47 g, 48% yield) D.C.I.M.S. 234(M+H) M.P. 80°-82° C.

Provenance & Evidence