Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Mandelic Acid | HCID 1292 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 178488037 | HCID 178488037 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Diethyl [S-(R*,R*)]-tartrate | HCID 117410 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 178488147 | HCID 178488147 | — |
Reaction Steps
Omeprazole sodium (500 grams) was suspended in acetone (6.0 liters) and diethyl D-tartrate (280 grams), titanium (IV) isopropoxide (325 grams) and triethylamine (410 grams) were added sequentially at a temperature of 35-40° C. L (+) mandelic acid (207 grams) was then added and further stirred for 30-60 minutes. The separated solid was filtered, washed with acetone (500 ml) and suck dried under vacuum. The wet solid thus resulting was suspended in a mixture of dichloromethane (2.0 liters) and 5% sodium bicarbonate solution (2.0 liters) and stirred for 15-30 minutes. The dichloromethane layer was separated from the resulting solution and the solvent was distilled off up to substantial completion to get the title compound in residual mass. [Weight: 180 grams, Chiral Purity: 99.93% (S-Isomer)].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07612098B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-00feb641baf94fa084185912f579c095 |
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| Source note | uspto-grants-2009_11 |
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