Methanol → HCID 178488037, compound

Participants

Reaction Steps

A solution of esomeprazole (9.5 g, 27.5 mmol; 2.3% sulfone, 2.3% R-enantiomer) in methyl isobutyl ketone (60 mL) was cooled to 15° C. 30% sodium methoxide in methanol (5.2 mL, 28.0 mmol) was added in 15 min. The addition funnel was rinsed with MeOH (0.3 mL) and methyl isobutyl ketone (0.7 mL). The mixture was stirred for 15 min and acetone (60 mL) was added slowly over 15 min. Subsequently, the solution was stirred at 25° C. A solid started to crystallize. After 1 h stirring, methyl tert-butyl ether (15 mL) was added dropwise. The resulting slurry was stirred overnight. The solid was collected by filtration, rinsed with acetone (2×15 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 6.3 g (62%). Sulfone content: 0.23%.

Provenance & Evidence