m-Chloroperbenzoic acid → HCID 22241471, compound

HRID 892208Notes

Reaction equation

HRID 892208 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=3)[CH:29]=2)[C:14]=1[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16]>ClCCl>[CH3:12][C:13]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][S:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=3)[CH:29]=2)=[O:9])[C:14]=1[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22241381HCID 22241381, compound

Product 1

HCID 22241471HCID 22241471, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (<86%, 34 mg, 0.17 mmol) is added to a solution of isobutyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenylsulfanylmethyl]-benzoate (80 mg, 0.17 mmol, example 84) in dichloromethane (1 mL) and the reaction is stirred overnight. The reaction is partitioned between ethyl acetate and sodium bicarbonate and the organic phase is washed with additional bicarbonate solution, dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 40% ethyl acetate in hexanes) to provide the title compound. MS (ESD) 488 (M+H)+.

Workup

  1. customThe reaction is partitioned between ethyl acetate and sodium bicarbonate
  2. washthe organic phase is washed with additional bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-13c947c51de64b76b10b3f8aa4bb944b
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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