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

Participants

Reaction Steps

A mixture of omeprazole (5 g, 14.5 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (6.30 g, 21.7 mmol) was dissolved in a minimum of a toluene/heptane mixture (0.84:0.16, 190 ml) at 100° 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 a toluene/heptane mixture (3:1, 2×50 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (6.108 g, 91%, 96.3% e.e.) as an off-white powder.

Provenance & Evidence