Water → [5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid

HRID 1591561Notes

Reaction equation

HRID 1591561 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[O:15])=[CH:8][C:7]=1[CH3:33].COC1C(SCC2C=CC(C3C=CC(C(F)(F)F)=CC=3)=CC=2)=CC(C)=C(C=1)OCC(O)=O.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=O)C=CC=CC=1.O>ClCCl>[CH3:13][O:12][C:10]1[C:9]([S:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)=[O:15])=[CH:8][C:7]([CH3:33])=[C:6]([CH:11]=1)[O:5][CH2:4][C:3]([OH:34])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 9825600[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acidHCID 20827054[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid methyl ester2×

Product 1

HCID 22280006[5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid methyl ester (compound 51A) Example 4 (0.5 g, 1.0 mmol) was dissolved in 25 ml dichloromethane followed by the addition of 2-benzenesulfonyl-3-phenyl-oxaziridine (0.274, 1.04 mmol). The reaction was stirred 1 h. 10 ml water was added, the layers were separated, and dichloromethane solution was dried over anhydrous sodium sulfate, decanted, and concentrated. The product was recrystallized from ethyl acetate to give the title product. MS m/z 493 (M+1). Step 2. Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid (compound 51) The title compound was prepared in the manner analogous to Example 1 using 51A. 400 MHz 1H NMR (DMSO-d6) δ 7.83 (d, 2H, J=8.78 Hz), 7.76 (d, 2H, J=8.30 Hz), 7.59 (d, 2H, J=8.30 Hz), 7.11 (d, 2H, J=8.30 Hz), 7.02 (s, 1H), 6.64 (s, 1H), 4.79 (s, 2H), 4.20 (d, 1H, J=12.7 Hz), 3.91 (d, 1H, J=12.4 Hz), 3.76 (s, 3H), 2.03 (s, 3H). MS m/z 479 (M+1).

Workup

  1. customthe layers were separated
  2. dry with materialdichloromethane solution was dried over anhydrous sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3edcb1e8aeac494f80df58cb0fd667f8
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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