m-Chloroperbenzoic acid → HCID 86599516, compound

HRID 2221356Notes

Reaction equation

HRID 2221356 reaction equation
C(=O)([O-])[OH:2].[Na+].[CH2:6]([NH:13][C:14](=[O:28])[CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[O:22][C:21]([CH3:27])([CH3:26])[CH:20]=[CH:19]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C=C(Cl)C=C(C(OO)=O)C=1>ClCCl>[CH2:6]([NH:13][C:14](=[O:28])[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[O:22][C:21]([CH3:26])([CH3:27])[CH:20]3[O:2][CH:19]3[C:18]=2[CH:17]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 69061253HCID 69061253, compound

Product 1

HCID 86599516HCID 86599516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

980 ml of a saturated aqueous sodium hydrogen carbonate solution was added to a solution of 28 g of the N-benzyl-2-(2,2-dimethyl-2H-chromen-6-yl)acetamide obtained above in 480 ml dichloromethane. A total of 44.1 g MCPBA in three 14.7 g portions was added to this receiving solution at 5 min. intervals, and the mixture was stirred for 18 hours at room temperature. The organic phase was separated, extracted once with 200 ml of a saturated aqueous sodium hydrogen carbonate solution, and the organic phase was then substantially completely evaporated at reduced pressure. 35 g N-benzyl-2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl)acetamide was obtained as crude oil, which was used without further purification or characterization for the subsequent reaction.

Workup

  1. customThe organic phase was separated
  2. extractionextracted once with 200 ml of a saturated aqueous sodium hydrogen carbonate solution
  3. customthe organic phase was then substantially completely evaporated at reduced pressure

Sources & evidence

ORD record
ord-ca46d9da433e498ba9607aaa847c8372
Source dataset
uspto-grants-2008_05
Patent number
US07368582B2

Reaction notes

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