Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoate → 3-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]phenyl)-2-methylpropanoic acid

HRID 2177240Notes

Reaction equation

HRID 2177240 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([CH3:37])[C:32]([O:34]CC)=[O:33])=[CH:26][CH:25]=1>>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([CH3:37])[C:32]([OH:34])=[O:33])=[CH:26][CH:25]=3)=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 20748401Ethyl 3-(4-hydroxyphenyl)-2-methylpropanoateHCID 90418265HCID 90418265, compound

Product 1

HCID 904176333-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]phenyl)-2-methylpropanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 following Steps 5 and 6 by coupling (3-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxyphenyl)-2-methyl-propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ: 7.71 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.16 (d, J=8.4 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 5.09 (s, 2H), 2.93-2.98 (m, 1H), 2.63-2.74 (m, 2H), 1.15 (d, J=6.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H17ClF3NO3S, 454.0 (M−H). found 454.0.

Workup

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

Sources & evidence

ORD record
ord-e2a80bd77d6b4805ad09b0bf79f56835
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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