Triethylamine → HCID 53671572, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 17β-hydroxymethyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (2.03 g, 5.04 mmol) prepared in example 3, part 15, in dichloromethane (50 mL) is treated with triethylamine (0.88 mL, 6.3 mmol), DMAP (0.155 g, 1.27 mmol) and methanesulfonyl chloride (0.43 mL, 5.6 mmol). After 3 hrs, the reaction is diluted with dichloromethane (50 mL), washed with 1N HCl, saturated aqueous NaCl and dried over MgSO4. Concentration gives a white foam which is dissolved in dimethylformamide (50 mL), treated with sodium azide (0.94 g, 14.5 mmol) and heated to 75° C. for 16 hrs. The reaction is poured into ethyl acetate, washed with water (5×100 mL), dried over MgSO4, concentrated and chromatographed on silica gel (20% ethyl acetate/hexane) to give 17β-azidomethyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one as a white foam of sufficient purity to carry on to the next step.

Provenance & Evidence