m-Chloroperbenzoic acid → 1-{4'-[3-Methyl-4-(2-phenyl-ethanesulfinylmethyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

HRID 1528779Notes

Reaction equation

HRID 1528779 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:17]([CH2:18][S:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:16]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4([C:43]([OH:45])=[O:44])[CH2:42][CH2:41]4)=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[O:15][N:14]=1>C(Cl)Cl>[CH3:12][C:13]1[C:17]([CH2:18][S:19]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:9])=[C:16]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:35]=[CH:36][C:37]([C:40]4([C:43]([OH:45])=[O:44])[CH2:41][CH2:42]4)=[CH:38][CH:39]=3)=[CH:30][CH:29]=2)[O:15][N:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 513523511-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

Product 1

HCID 665782631-{4'-[3-Methyl-4-(2-phenyl-ethanesulfinylmethyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (0.023 g, 0.11 mmol) was added to a solution of 1-[4′-(3-methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid (0.050 g, 0.11 mmol) in CH2Cl2. After stirring for 15 minutes the mixture was concentrated and the residue was purified by preparative HPLC to give the title compound.

Workup

  1. concentrationwas concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-27999db73b404c34ae4e95df2e5b0aba
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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