Iodoethane → HCID 86656361, compound

HRID 1942512Notes

Reaction equation

HRID 1942512 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:12]2[CH:13]=[C:14]([C:21]([NH:23][C@@H:24]3[C@H:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:28][CH2:27][N:26]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:25]3)=[O:22])[C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=2[O:10][C:9]([CH3:44])([CH3:43])[C:8]1=[O:45].[H-].[Na+].[CH2:48](I)[CH3:49].[Cl-].[NH4+]>CN(C=O)C>[CH2:48]([N:23]([C:21]([C:14]1[C:15]([C:17]([F:18])([F:20])[F:19])=[CH:16][C:11]2[O:10][C:9]([CH3:44])([CH3:43])[C:8](=[O:45])[N:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]=2[CH:13]=1)=[O:22])[C@@H:24]1[C@H:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:28][CH2:27][N:26]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:25]1)[CH3:49]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67332148HCID 67332148, compound

Product 1

HCID 86656361HCID 86656361, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (3R,4S)-3-({[4-(4-methoxybutyl)-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}amino)-4-phenylpiperidine-1-carboxylate (386 mg) in DMF (1 ml) was added sodium hydride (48.7 mg) at 0° C., and the mixture was stirred for 10 minutes. To the mixture was added ethyl iodide (126 μl), and the mixture was stirred at room temperature for 5 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water (×2) and a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=3/1) to give the title compound (128 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water (×2)
  4. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-8dca047b29804242a47edc7ddb671181
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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