Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (S)-mandelic acid | HCID 439616 | — |
| Reactant | diethyl-D-tartarate | HCID 29414049 | — |
| Reactant | HCID 178488156 | HCID 178488156 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 178488147 | HCID 178488147 | — |
Reaction Steps
The procedure was carried out as described in Raju et al, Organic Process Research & Development 2006, 10, 33-35, which is hereby incorporated by reference in its entirety. To a suspension of omeprazole sodium salt (5.53 g, 15.1 mmol, 1 equiv) in acetone (60 mL), were added a solution of diethyl-D-tartrate (3.1 g, 15.1 mol, 1 equiv) in acetone (3 mL), titanium (IV) isopropoxide (2.14 g, 7.55 mmol, 0.5 equiv) and triethylamine (4.75 g, 45.3 mmol, 3 equiv) at 35-40° C. To the resulting homogeneous solution was added L-(+)-mandelic acid (2.64 g, 17.4 mmol, 1.15 equiv). The mixture was cooled to ambient temperature and stirred for about 1-2 hours. The precipitate was filtered, washed with acetone (30 mL), and dried under reduced pressure to afford esomeprazole mandalate salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07598273B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-a331987f5f5c4b39ac0b2dead2adf1b7 |
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| Source note | uspto-grants-2009_10 |
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