Acetonitrile → HCID 67330942, compound

HRID 1942456Notes

Reaction equation

HRID 1942456 reaction equation
[CH3:1][C:2]1([CH3:36])[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[C:10]([C:17]([N:19]([CH:33]([CH3:35])[CH3:34])[C@@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)=[O:18])[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:4]=2[O:3]1.[CH2:37]([O:39][C:40](=[O:44])[CH2:41][CH2:42]Br)[CH3:38].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH2:37]([O:39][C:40](=[O:44])[CH2:41][CH2:42][N:6]1[C:5]2[CH:9]=[C:10]([C:17]([N:19]([CH:33]([CH3:34])[CH3:35])[C@@H:20]3[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)=[O:18])[C:11]([C:13]([F:14])([F:15])[F:16])=[CH:12][C:4]=2[O:3][C:2]([CH3:36])([CH3:1])[C:7]1=[O:8])[CH3:38]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 67330735HCID 67330735, compound

Product 1

HCID 67330942HCID 67330942, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To tert-Butyl (3R)-3-[{[2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (460 mg) were added 3-bromopropionic acid ethyl ester (0.19 ml), potassium carbonate (298 mg) and acetonitrile (5 ml), and the mixture was refluxed for 5 hours. After the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate solution. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (350 mg) as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate solution
  3. washThe obtained ethyl acetate solution was washed with water
  4. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2d4dfdfa5a214efd828b3be80ca7d207
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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