Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66976736 | HCID 66976736 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66976169 | HCID 66976169 | 82.1% |
Reaction Steps
Trifluoroacetic anhydride (0.080 mL, 0.57 mmol) was added to a solution of tert-butyl (6R,7R)-6-[(4-carbamoyl-1,3-thiazol-2-yl)methyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (126 mg, 0.26 mmol) and pyridine (0.084 mL, 1.04 mmol) in THF (4 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, triethylamine (0.144 mL, 1.04 mmol) and trifluoroacetic anhydride (0.080 mL, 0.57 mmol) were added, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (100 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-36d72147003749428ba6392ff9d6db28 |
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| Source note | uspto-grants-2014_05 |
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