HCID 66976330, compound → HCID 66975233, compound

HRID 1022595Notes

Reaction equation

HRID 1022595 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:23][O:24]C3C=CC(OC)=CC=3)[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:23][OH:24])[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 66976330HCID 66976330, compound

Product 1

HCID 66975233HCID 66975233, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (2RS)-2-(3,4-dichlorophenyl)-2-[(4-methoxyphenoxy)methyl]-1,4-oxazepane-4-carboxylate (3.18 g) in acetonitrile (80 ml) and water (20 mL) was added ceric ammonium nitrate (10.8 g) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.9 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe obtained extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b296efbce781474596d812761e697830
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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