HCID 66976010, compound → HCID 66975608, compound

HRID 1022590Notes

Reaction equation

HRID 1022590 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:23][O:24]C3C=CC(OC)=CC=3)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]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])[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 66976010HCID 66976010, compound

Product 1

HCID 66975608HCID 66975608, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (7RS)-7-(3,4-dichlorophenyl)-7-[(4-methoxyphenoxy)methyl]-1,4-oxazepane-4-carboxylate (4.75 g) in acetonitrile (70 mL) and water (14 mL) was added ceric ammonium nitrate (16.18 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. 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 (ethyl acetate/hexane) to give the title compound (3.36 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 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c78b924858114bf6bdbd4ea18b80f0aa
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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