m-Chloroperbenzoic acid → [5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid

HRID 1591560Notes

Reaction equation

HRID 1591560 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)(=[O:16])=[O:15])=[CH:8][C:7]=1[CH3:34].COC1C(SCC2C=CC(C3C=CC(C(F)(F)F)=CC=3)=CC=2)=CC(C)=C(C=1)OCC(O)=O.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH3:13][O:12][C:10]1[C:9]([S:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)(=[O:16])=[O:15])=[CH:8][C:7]([CH3:34])=[C:6]([CH:11]=1)[O:5][CH2:4][C:3]([OH:35])=[O:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 9825600[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acidHCID 20827055[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid methyl ester3×

Product 1

HCID 10311231[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid methyl ester (compound 50A) Example 4 (200 mg) was dissolved in 5 ml dichloromethane. Excess m-chloroperbenzoic acid (300 mg) was added and the reaction was allowed to stir 3 h. The solvent was removed under vacuum and the crude product was purified by MPLC. MS m/z 509 (M+1). Step 2. Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid (compound 50) The title compound was prepared in the manner analogous to Example 1 using 50A. 400 MHz 1H NMR (DMSO-d6) δ 13.13 (br(s), 1H), 7.85 (d, 2H, J=8.1 Hz), 7.77 (d, 2H, J=8.3 Hz), 7.66 (d, 2H, J=8.6 Hz), 7.3 (m, 3H), 6.76 (s, 1H), 4.89 (s, 2H), 4.67 (s, 2H), 3.96 (s, 3H), 2.04 (s, 3H). MS m/z 495 (M+1).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude product was purified by MPLC
  3. customPreparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfonyl)-phenoxy]-acetic acid (compound 50) The title compound

Sources & evidence

ORD record
ord-42d47eb63e404caa97a74a7cf3b1d044
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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