Water → HCID 66976057, compound

HRID 1022764Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH:10][CH2:11][C@H:12]1[C@H:18]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=2)[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13]1)=[O:9].C(N(CC)CC)C.[C:41](=O)(OC(Cl)(Cl)Cl)[O:42]C(Cl)(Cl)Cl.O>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@@H:18]2[O:17][CH2:16][CH2:15][N:14]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13][C@H:12]2[CH2:11][N:10]2[C:8](=[O:9])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:1][C:41]2=[O:42])=[CH:20][C:21]=1[F:26]

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

temperatureto cool to room temperature
customthe mixture was partitioned twice with ethyl acetate
washthe mixture was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6a1c2bce94c84e96ad3729e8ae9bdb79
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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