3-(4-Hydroxy-2-trifluoromethyl-phenyl)-propionic acid ethyl ester → 3-(4-[[3-(2-Fluoro-4-methylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2-(trifluoromethyl)phenyl)propanoic acid

HRID 2177189Notes

Reaction equation

HRID 2177189 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([CH2:14][OH:15])=[C:12]([C:16]([F:19])([F:18])[F:17])[S:11][N:10]=1.O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:23]([C:34]([F:37])([F:36])[F:35])[CH:22]=1>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[C:23]([C:34]([F:35])([F:37])[F:36])[CH:22]=2)=[C:12]([C:16]([F:19])([F:17])[F:18])[S:11][N:10]=1

Participants

3

Reactant 2

HCID 587538593-(4-Hydroxy-2-trifluoromethyl-phenyl)-propionic acid ethyl esterHCID 90418878(3-(2-Fluoro-4-methylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methanol

Product 1

HCID 904179653-(4-[[3-(2-Fluoro-4-methylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-2-(trifluoromethyl)phenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methanol and ethyl 3-(4-hydroxy-2-(trifluoromethyl)phenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 7.39-7.34 (m, 2H), 7.16 (d, J=7.6 Hz, 1H), 7.07 (d, J=10.0 Hz, 1H), 6.96 (d, J=8.8 Hz, 1H), 6.89 (d, J=2.4 Hz, 1H), 5.18 (s, 2H), 3.01 (t, J=7.6 Hz, 2H), 2.44 (t, J=8.4 Hz, 2H), 2.43 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H16F7NO3S, 506.1 (M−H). found 506.1.

Workup

  1. customThe title compound was prepared
  2. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-38ec2066b40340fc99f1b6b8ed6bb477
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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