Water → HCID 66976187, compound

HRID 1022794Notes

Reaction equation

HRID 1022794 reaction equation
Cl[S:2]([CH2:5][C@H:6]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][C@H:7]1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)(=[O:4])=[O:3].C(N(CC)CC)C.[CH:35]([NH2:38])([CH3:37])[CH3:36].O>C(OCC)(=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([C@H:7]2[C@@H:6]([CH2:5][S:2](=[O:4])(=[O:3])[NH:38][CH:35]([CH3:37])[CH3:36])[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 8471TriethylamineHCID 86663877HCID 86663877, compound

Product 1

HCID 66976187HCID 66976187, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7S)-7-[(chlorosulfonyl)methyl]-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (95 mg) in ethyl acetate (2.0 mL) were added triethylamine (0.06 mL) and isopropylamine (0.03 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (33 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-15831dce00ed474d98ec8225dfb60b61
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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