Dimethyl Sulfoxide → HCID 57314607, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution (-78° C.) of oxalyl chloride (1.5 ml of 2M solution in CH2Cl2) was added dimethyl sulfoxide (361 mg) dropwise, followed by a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-14-triisopropylsiloxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (947 mg) in dry methylene chloride (3 ml). The reaction mixture was stirred for 30 min. at -78° C. and then triethylamine (1 ml) was added. The reaction temperature was raised to room temperature, reaction was poured into water (20 ml), and extracted with ethyl acetate (three times). Combined organic layers were washed (water, sat'd NaHCO3), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography, 40% ethyl acetate: 60% hexane) gave 870 mg of the title compound.

Provenance & Evidence