P-Toluic Acid → HCID 86647591, compound

Participants

Reaction Steps

4-Methylbenzoic acid (p-toluic acid) (0.22 g, 1.6 mmol) (0.16 g, 1.6 mmol) was added to the stirred solution of 17-oximino-5-androsten-3β-ol (9) (0.5 g, 1.6 mmol) and dicyclohexylcarbodiimide (DCC) (0.34 g, 1.6 mmol) in anhydrous dichloromethane (30.0 ml). The reaction mixture was stirred for 48 hr at room temperature (20-25°) and completion of the reaction was monitored by TLC. The precipitated dicyclohexylurea (DCU) was filtered, solvent removed under vacuum and the residue was crystallized from ethyl acetate:petroleum ether (60:80) to obtain 12 (0.29 g, 58.0%) mp 135-139° C.

Provenance & Evidence