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

Participants

Reaction Steps

A mixture of omeprazole (500 mg, 1.45 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (630 mg, 2.17 mmol, 99.3% e.e. recovered according to Example 24) was dissolved in a minimum volume of toluene (18 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 toluene (2×5 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (627 mg, 94%, 93.7% e.e.) as an off-white powder.

Provenance & Evidence