m-Chloroperbenzoic acid → HCID 87078300, compound

HRID 416011Notes

Reaction equation

HRID 416011 reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][N:5](C)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([CH2:21][CH:22]3[CH2:26][CH2:25][N:24]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:23]3=[O:33])=[C:16]([Cl:34])[CH:15]=2)=[CH:10][CH:9]=1)=[O:7].ClC1C=C(C=CC=1)C(OO)=[O:42]>ClCCl>[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][NH+:5]([O-:42])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([CH2:21][CH:22]3[CH2:26][CH2:25][N:24]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:23]3=[O:33])=[C:16]([Cl:34])[CH:15]=2)=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57741485HCID 57741485, compound

Product 1

HCID 87078300HCID 87078300, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve racemic 3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carboxylic acid (2-dimethylamino-ethyl)-methyl-amide (0.097 g, 0.183 mmol) in dichloromethane (5 mL) under argon atmosphere. Add 3-chloroperoxybenzoic acid (0.045 g, 0.200 mmol) and stir at room temperature for 1 hour. Concentrate under reduced pressure and purify via flash chromatography by eluding with gradient (100%) dichloromethane to 25% methanol/75% dichloromethane to obtain 0.086 g (87%) of a white solid: MS (m/z): 546 (M+).

Workup

  1. concentrationConcentrate under reduced pressure
  2. custompurify via flash chromatography

Sources & evidence

ORD record
ord-ee3c80d27cf54410a239dd8cc0507ebb
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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