Water → HCID 66975649, compound

HRID 1022821Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][NH:19][C:18]3=[O:23])[O:14][CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].[CH3:33]I.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][N:17]3[CH2:22][CH2:21][CH2:20][N:19]([CH3:33])[C:18]3=[O:23])[O:14][CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-[(2-oxotetrahydropyrimidin-1(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate (300 mg) in DMF (3 mL) was added sodium hydride (60% in oil, 31 mg), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added dropwise methyl iodide (190 mg), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, 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 (180 mg).

Workup

stirringthe mixture was stirred at room temperature for 1 hr
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f9eae56af83c4af0aa5f7586c5288df2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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