m-Chloroperbenzoic acid → HCID 118666092, compound

HRID 630476Notes

Reaction equation

HRID 630476 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34]([N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[O:35])[CH:32]=4)[C:27]([S:42][CH3:43])=[CH:26]3)=[N:23][CH:24]=2)=[CH:15][CH:14]=1>ClCCl.CN(C=O)C.ClCCl>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[N:23][C:22]([N:25]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:34]([N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[O:35])[CH:32]=4)[C:27]([S:42]([CH3:43])=[O:6])=[CH:26]3)=[N:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118666174HCID 118666174, compound

Product 1

HCID 118666092HCID 118666092, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

m-Chloroperoxybenzoic acid (134 mg, 0.5022 mmol, 0.8 eq) was added at 0° C. to a stirred solution of 86a) (280 mg, 0.6278 mmol, 1.0 eq) in dichloromethane/DMF (10:1; 22 mL) and the solution was stirred for 1 h at this temperature. The reaction mixture was then diluted with dichloromethane (20 mL), washed with saturated sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvents were removed under vacuum and the residue was purified by preparative TLC using ethyl acetate as eluent. White solid. Yield: 65 mg (21% of theory)

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvents were removed under vacuum
  4. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-214de0c3f96e41b78b681d12c6e6d9ff
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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