Water → HCID 66976772, compound

HRID 1022815Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([CH2:16]I)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]1=[O:31].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:15]([CH2:16][N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]3=[O:31])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-(iodomethyl)-1,4-oxazepane-4-carboxylate (370 mg) in DMF (8.0 mL) were added 2(1H)-pyridinone (87 mg) and potassium carbonate (158 mg), and the mixture was heated at 80° C. for 4 hr. The reaction solution was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.1 N hydrochloric acid and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (44 mg).

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with 0.1 N hydrochloric acid and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-14fa6dbcaa984a549c78f3fe181604ed
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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