Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 66976469 | HCID 66976469 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66976057 | HCID 66976057 | 96.2% |
Reaction Steps
To a solution of tert-butyl (6R,7R)-6-({[(2-aminophenyl)carbonyl]amino}methyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (191.1 mg) and triethylamine (167 μL) in THF (5 mL) was added bis(trichloromethyl) carbonate (142 mg) at 0° C., and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and poured into water, and the mixture was partitioned twice with ethyl acetate. The organic layers were combined, and the mixture was washed with brine, and dried over anhydrous magnesium 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 (193.8 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-6a1c2bce94c84e96ad3729e8ae9bdb79 |
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| Source note | uspto-grants-2014_05 |
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