Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → 3-(3,5-Difluoro-4-[[5-(trifluoromethyl)-3-[4-(trifluoromethyl)phenyl]-1,2-thiazol-4-yl]methoxy]phenyl)propanoic acid

HRID 2177166Notes

Reaction equation

HRID 2177166 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:27]1[C:32]([F:33])=[CH:31][C:30]([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[CH:29][C:28]=1[F:41]>>[F:33][C:32]1[CH:31]=[C:30]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH:29]=[C:28]([F:41])[C:27]=1[O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13]

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418158HCID 90418158, compound

Product 1

HCID 904184763-(3,5-Difluoro-4-[[5-(trifluoromethyl)-3-[4-(trifluoromethyl)phenyl]-1,2-thiazol-4-yl]methoxy]phenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (5-(trifluoromethyl)-3-(4-(trifluoromethyl)phenyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxy-3,5-difluorophenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 7.99 (d, J=8.1 Hz, 2H), 7.82 (d, J=8.1 Hz, 2H), 6.86 (d, J=13.5 Hz, 2H), 5.23 (s, 2H), 2.87 (t, J=7.2 Hz, 2H), 2.60 (t, J=7.5 Hz, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H13F8NO3S, 510.1 (M−H). found 509.9.

Workup

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

Sources & evidence

ORD record
ord-50d755e63832430aad3211c374035a45
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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