Water → HCID 66975055, compound

HRID 1022574Notes

Reaction equation

HRID 1022574 reaction equation
[O:1]=[C:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[Cl:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[CH:21][C:22]=1[Cl:23].C1COCC1.O>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]([C:2]2([OH:1])[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]2)[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

5

Reactant 3

HCID 962WaterHCID 24865325tert-Butyl 6-oxo-1,4-oxazepane-4-carboxylateHCID 178420679HCID 178420679, compound

Product 1

HCID 66975055HCID 66975055, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 6-oxo-1,4-oxazepane-4-carboxylate (418 mg) prepared by the method described in WO2004/074291 in THF (12 mL) was added 0.5 M 3,4-dichlorophenylmagnesium bromide-THF (4.7 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1.5 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with dil. hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (455 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with dil. hydrochloric acid, saturated aqueous sodium hydrogen carbonate, 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 column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7ecb83d80c5c47a9a7ec49b2f819293f
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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