m-Chloroperbenzoic acid → HCID 23143250, compound

HRID 732214Notes

Reaction equation

HRID 732214 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:18][C:19]1[CH:38]=[CH:37][C:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.ClC1C=CC=C(C(OO)=[O:47])C=1>O1CCCC1>[CH3:1][S:2]([CH2:3][CH2:4][CH2:5][N:6]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:30]=2)=[CH:37][CH:38]=1)[C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:11]=1)=[O:47]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23143243HCID 23143243, compound

Product 1

HCID 23143250HCID 23143250, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-{4-[(4-{[[3-(methylthio)propyl](4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}-propanoate (280 mg), m-chloroperbenzoic acid (122 mg) and tetrahydrofuran (10 mL) was stirred at room temperature for 3 hr. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:0 in volume ratio) to give the title compound (180 mg, yield 62%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:0 in volume ratio)

Sources & evidence

ORD record
ord-ad4e77148c4d47a39502e9af1d3227ca
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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