(4-Mercapto-5-methoxy-2-methyl-phenoxy)-acetic Acid Methyl Ester → [5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid

HRID 1591554Notes

Reaction equation

HRID 1591554 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([SH:14])=[CH:8][C:7]=1[CH3:15].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[CH:21][C:20]=1[CH3:35].COC1C(S(C)CC2C=CC(C3C=CC(C(F)(F)F)=CC=3)=CC=2)=CC(C)=C(C=1)OCC(O)=O>>[CH3:13][O:12][C:10]1[C:9]([S:14][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=3)=[CH:21][C:20]=2[CH3:35])=[CH:8][C:7]([CH3:15])=[C:6]([CH:11]=1)[O:5][CH2:4][C:3]([OH:2])=[O:16]

Participants

4

Reactant 3

HCID 11311052(4-Mercapto-5-methoxy-2-methyl-phenoxy)-acetic Acid Methyl EsterHCID 222801404-Chloromethyl-3-methyl-4'-trifluoromethyl-biphenylHCID 178493544HCID 178493544, compound2×

Product 1

HCID 10288768[5-Methoxy-2-methyl-4-(3-methyl-4'-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid

Procedure

Preparation of (3-Methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (compound 39A) The title compound was prepared in the manner analogous to Example 3A using (4-bromo-2-methyl-phenyl)-methanol and 4-(trifluoromethyl)benzeneboronic acid. MS m/z 249 (M-OH). Step 2. Preparation of 4chloromethyl-3-methyl-4′-trifluoromethyl-biphenyl (compound 39B) The title compound was prepared in the manner analogous to Example 3B using 39A. 400 MHz 1H NMR (DMSO-d6) δ 7.84 (d, 2H, J=8.3 Hz), 7.76 (d, 2H, J=8.3 Hz), 7.57 (s, 1H), 7.48 (m, 2H), 4.80 (s, 2H), 2.41 (s, 3H). Step 3. Preparation of [5-Methoxy-2-methyl-4-(3-methyl-4′-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid methyl ester (compound 39C) The title compound was prepared in the manner analogous to Example 1F using 1D and 39B. MS m/z 491 (M+1). Step 4. Preparation of [5-Methoxy-2-methyl-4-(methyl-4′-trifluoromethyl-biphenyl-4-ylmethylsulfanyl)-phenoxy]-acetic acid (compound 39) The title compound was prepared in the manner analogous to Example 1 using 39C. IR cm−1: 1740, 1322; 400 MHz 1H NMR (DMSO-d6) δ 7.81 (d, 2H, J=8.1 Hz), 7.73 (d, 2H, J=8.1 Hz), 7.51 (s, 1H), 7.39 (d, 1H, J=7.8 Hz), 7.16 (d, 1H, J=7.8 Hz), 7.04 (s, 1H), 6.53 (s, 1H), 4.71 (s, 2H), 4.00 (s, 2H), 3.73 (s, 3H), 2.39 (s, 3H), 2.02 (s, 3H); MS m/z 477 (M+1). Anal. Calc'd for C25H23F3O4S.0.1 H2O; C, 62.78; H, 4.89; found: C, 62.57; H, 4.82.

Workup

  1. customwas prepared in the manner analogous to Example 1F

Sources & evidence

ORD record
ord-10aa875a46f849cbb03202dbb9b419e6
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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