m-Chloroperbenzoic acid → HCID 22241458, compound

HRID 892209Notes

Reaction equation

HRID 892209 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:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH:30]=2)=[O:28])[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:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][C:37]3[CH:46]=[CH:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH:30]=2)(=[O:9])=[O:28])[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 22241471HCID 22241471, compound

Product 1

HCID 22241458HCID 22241458, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (<86%, 62 mg, 0.31 mmol) is added to a solution of isobutyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenylsulfanylmethyl]-benzoate (73 mg, 0.16 mmol, example 85) 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, 30% ethyl acetate in hexanes) to provide the title compound. MS (ESI) 504 (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, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-34f3d5614da4440c87a9cd4f80f195f9
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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