Sodium hydride → HCID 66975082, compound

HRID 1022758Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][NH:23][C:24](=[O:30])[NH:25][CH2:26][CH2:27][CH2:28]Cl)=[CH:4][C:3]=1[F:31].[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C@H:9]2[CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][NH:25][C:24]2=[O:30])=[CH:4][C:3]=1[F:31]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-({[(3-chloropropyl)carbamoyl]amino}methyl)-1,4-oxazepane-4-carboxylate (531 mg) in DMF (22 mL) was added sodium hydride (48.8 mg, 60% in oil) under ice-cooling, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (563 mg).

Workup

temperaturecooling
additionTo the reaction mixture was added
distillationdistilled water
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with distilled water and brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-32a2735ffd704c19b72fcaddfc24cfb2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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