Methyl iodide → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[methyl(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylate

HRID 1022721Notes

Reaction equation

HRID 1022721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[C:23](=[O:29])[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:30](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[C:23](=[O:29])[N:24]([CH3:30])[S:25]([CH3:28])(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66975840tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976015tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[methyl(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylateYield 68.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)carbamoyl]-1,4-oxazepane-4-carboxylate (246 mg) in DMF (3 mL) were added potassium carbonate (109 mg) and methyl iodide (0.049 mL) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (174 mg).

Workup

  1. washThe diluted solution was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e6fb2b4b84724e948311e4dbdfc3437e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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