Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate → 3-(3,5-Difluoro-4-((4-(4-methoxyphenyl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)phenyl)propanoic acid
Reaction equation
CS(OCC1C(C2C=CC(OC)=CC=2)=CSC=1C(F)(F)F)(=O)=O.FC1C=C(O)C=C(F)C=1CCC(OCC)=O.[F:40][C:41]1[CH:42]=[C:43]([CH2:67][CH2:68][C:69]([O:71]CC)=[O:70])[CH:44]=[C:45]([F:66])[C:46]=1[O:47][CH2:48][C:49]1[C:53]([C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=2)=[CH:52][S:51][C:50]=1[C:62]([F:65])([F:64])[F:63]>>[F:40][C:41]1[CH:42]=[C:43]([CH2:67][CH2:68][C:69]([OH:71])=[O:70])[CH:44]=[C:45]([F:66])[C:46]=1[O:47][CH2:48][C:49]1[C:53]([C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=2)=[CH:52][S:51][C:50]=1[C:62]([F:64])([F:65])[F:63]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared according to the procedure described in Example 182 by coupling of [4-(4-methoxyphenyl)-2-(trifluoromethyl)thiophen-3-yl]methyl methanesulfonate and ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis of ethyl 3-(3,5-difluoro-4-((4-(4-methoxyphenyl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)phenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=7.0 Hz, 2H), 7.38 (s, 1H), 6.95 (d, J=6.5 Hz, 2H), 6.72 (d, J=7.0 Hz, 1H), 5.08 (s, 2H), 3.85 (s, 3H), 2.90 (t, J=5.5 Hz, 2H), 2.66 (t, J=6.8 Hz, 2H). LCMS (ESI, M/Z) for C22H17F5O4S: 473.1 (MH+).
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-81060cd0f3d548ee8e0b1175e1e09140
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067898B1
Reaction notes
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