Water → HCID 86656373, compound

HRID 1942551Notes

Reaction equation

HRID 1942551 reaction equation
[CH2:1]([N:5]1[C:10]2[CH:11]=[C:12]([C:19]([N:21]([CH:35]([CH3:37])[CH3:36])[C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]3)=[O:20])[C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:9]=2[O:8][C:7]([CH3:39])([CH3:38])[C:6]1=[O:40])[CH2:2][CH:3]=[CH2:4].ClC1C=CC=C(C(OO)=[O:49])C=1.O>ClCCl>[CH3:39][C:7]1([CH3:38])[C:6](=[O:40])[N:5]([CH2:1][CH2:2][CH:3]2[CH2:4][O:49]2)[C:10]2[CH:11]=[C:12]([C:19]([N:21]([CH:35]([CH3:36])[CH3:37])[C@@H:22]3[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:23]3)=[O:20])[C:13]([C:15]([F:17])([F:16])[F:18])=[CH:14][C:9]=2[O:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 67331220HCID 67331220, compound

Product 1

HCID 86656373HCID 86656373, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3R)-3-[{[4-but-3-en-1-yl-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (1.7 g) in dichloromethane (15 ml) was added m-chloroperbenzoic acid (775 mg), and the mixture was stirred at room temperature overnight. To the reaction solution was added water, and the mixture was extracted with chloroform. The extract was washed with 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 (hexane/ethyl acetate) to give the title compound (780 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-af0106623b1a42d98224ef46f6e9fe74
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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