Water → HCID 66975792, compound

HRID 1022781Notes

Reaction equation

HRID 1022781 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C@H:11]2[C@@H:17]([CH2:18][NH:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])[O:16][CH2:15][CH2:14][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10].[CH3:32]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C@H:11]2[C@@H:17]([CH2:18][N:19]([C:20](=[O:24])[CH2:21][O:22][CH3:23])[CH3:32])[O:16][CH2:15][CH2:14][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66976633HCID 66976633, compound

Product 1

HCID 66975792HCID 66975792, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 16 mg) was added to a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-{[(methoxyacetyl)amino]methyl}-1,4-oxazepane-4-carboxylate (180 mg) in DMF (5 ml), and the mixture was stirred at room temperature for 20 min. Methyl iodide (57 mg) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature overnight. 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 (170 mg).

Workup

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

Sources & evidence

ORD record
ord-e2dc92eb11e94386bb5c0cef3e345202
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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