Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 178488147 | HCID 178488147 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | HCID 178488037 | HCID 178488037 | — |
Reaction Steps
A solution of esomeprazole (19.5 g, 56.5 mmol; 1.3% sulfone, 1.05% R-enantiomer) in methyl ethyl ketone (60 mL) and acetone (60 mL) was cooled to 15° C. 30% sodium methoxide in methanol (10.7 mL, 57.6 mmol) was added in 15 min. Subsequently, the solution was stirred at 27° C. A solid started to crystallize. The resulting slurry was stirred overnight at room temperature. The solid was collected by filtration, rinsed with acetone (2×20 mL) and dried under reduced pressure at 50° C. to yield esomeprazole sodium. Yield: 10.8 g (52%). Sulfone content: 0.05%. R-enantiomer content: 0.00%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680284B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-73b6bb94915b4d7aaeb75b39a681bccc |
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| Source note | uspto-grants-2014_03 |
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