Water → HCID 66976367, compound

HRID 1022789Notes

Reaction equation

HRID 1022789 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][NH:17][CH3:18])[O:14][CH2:13][CH2:12][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16][N:17]([CH3:18])[S:34]([CH3:33])(=[O:36])=[O:35])[O:14][CH2:13][CH2:12][N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66976506HCID 66976506, compound

Product 1

HCID 66976367HCID 66976367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[(methylamino)methyl]-1,4-oxazepane-4-carboxylate (150 mg) in THF (5 mL) were successively added dropwise triethylamine (0.070 mL) and methanesulfonyl chloride (0.036 mL), 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 (133 mg).

Workup

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

Sources & evidence

ORD record
ord-78b496acadc34a3fb6a8ae74852f341a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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