(2S)-1,1,2-Triphenyl-1,2-ethanediol → Esomeprazole

Participants

Reaction Steps

A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of methyl isobutyl ketone (8 ml) at 90° C. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with methyl isobutyl ketone (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (253 mg, 76%, 94% e.e.) as an off-white powder.

Provenance & Evidence