4-Toluenesulfonyl chloride → HCID 12790113, compound

Participants

Reaction Steps

A solution of 55.1 mg of p-toluenesulphonyl chloride in 0.2 ml. of dry pyridine was added at 0° C. to a solution of 100 mg of (20S)-1α,3β-diacetoxy-21-hydroxy-20-methyl-pregn-5-ene in 0.5 ml. of dry pyridine. After standing at 0° C. for 6 hours, the mixture was poured on to ice-water and extracted with ether. The extract was washed successively with 2-N hydrochloric acid, water, saturated sodium bicarbonate solution and water. The residue obtained after drying over sodium sulphate and concentration was chromatographed on 3.5 g of silica gel using hexane/ether (4:1) for the elution, there being obtained 100 mg of uniform (20S)-1α,3β-diacetoxy-20-methyl-21-(p-toluene-sulphonyloxy)-pregn-5-ene. After recrystallisation from ether, the product melted at 168°-170° C.; [α]D =-20.8° (c=0.5 in chloroform).

Provenance & Evidence