Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | HCID 66975558 | HCID 66975558 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66975425 | HCID 66975425 | 97.2% |
Reaction Steps
To a solution of sodium borohydride (49 mg) in THF (1.25 mL)-EtOH (0.9 mL) was added calcium chloride (72 mg), and the mixture was stirred at room temperature for 20 min. To this reaction mixture was added a solution of 4-tert-butyl 5-ethyl (5RS,6SR)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4,5-dicarboxylate (135 mg) in THF (1.25 ml), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (118 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722662B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-8f5415cf90ee48d383d92a11e99d131b |
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| Source note | uspto-grants-2014_05 |
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