Sodium methanolate methanol → HCID 66976578, compound

HRID 1022701Notes

Reaction equation

HRID 1022701 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[CH2:23][NH:24][S:25]([CH:28]=[CH2:29])(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:30][O-:31].[Na+].CO>CO.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[CH2:23][NH:24][S:25]([CH2:28][CH2:29][O:31][CH3:30])(=[O:26])=[O:27])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 66975627HCID 66975627, compound

Product 1

HCID 66976578HCID 66976578, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(ethenylsulfonyl)amino]methyl}-1,4-oxazepane-4-carboxylate (200 mg) in methanol (1 mL) was added 28% sodium methoxide-methanol (4 mL) solution at room temperature, and the mixture was stirred at 60° C. for 4 hr. 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 (132 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-7f53b789c166494ab045b164ab7bc1c9
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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