Water → tert-butyl (6SR,7SR)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)amino]-1,4-oxazepane-4-carboxylate

HRID 1022665

Reaction equation

HRID 1022665 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8]1.C(N(CC)CC)C.O>C1COCC1>[Cl:21][C:16]1[CH:15]=[C:14]([CH:13]2[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:8][CH:7]2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66975299tert-butyl (6SR,7SR)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976033tert-butyl (6SR,7SR)-7-(3,4-dichlorophenyl)-6-[(methylsulfonyl)amino]-1,4-oxazepane-4-carboxylateYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (34 mg) was added to a solution of tert-butyl (6SR,7SR)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (90 mg) and triethylamine (33 mg) in THF (5 mL), 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 (90 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-870da08f2e68436e8367b1e693122630
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Linked notes

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