Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate → 3-(4-((4-(Cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)-3,5-difluorophenyl)propanoic acid

HRID 2177328Notes

Reaction equation

HRID 2177328 reaction equation
CS(OCC1C(C2CCCC=2)=CSC=1C(F)(F)F)(=O)=O.FC1C=C(O)C=C(F)C=1CCC(OCC)=O.[C:37]1([C:42]2[C:43]([CH2:51][O:52][C:53]3[C:58]([F:59])=[CH:57][C:56]([CH2:60][CH2:61][C:62]([O:64]CC)=[O:63])=[CH:55][C:54]=3[F:67])=[C:44]([C:47]([F:50])([F:49])[F:48])[S:45][CH:46]=2)[CH2:41][CH2:40][CH2:39][CH:38]=1>>[C:37]1([C:42]2[C:43]([CH2:51][O:52][C:53]3[C:58]([F:59])=[CH:57][C:56]([CH2:60][CH2:61][C:62]([OH:64])=[O:63])=[CH:55][C:54]=3[F:67])=[C:44]([C:47]([F:49])([F:50])[F:48])[S:45][CH:46]=2)[CH2:41][CH2:40][CH2:39][CH:38]=1

Participants

4

Reactant 3

HCID 23082713Ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoateHCID 90418283(4-(Cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methyl methanesulfonateHCID 90418888Ethyl 3-(4-((4-(cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)-3,5-difluorophenyl)propanoate

Product 1

HCID 854714283-(4-((4-(Cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)-3,5-difluorophenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 183 by coupling of (4-(cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methyl methanesulfonate and ethyl 3-(2,6-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis of ethyl 3-(4-((4-(cyclopent-1-en-1-yl)-2-(trifluoromethyl)thiophen-3-yl)methoxy)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 6.76 (d, J=7.8 Hz, 2H), 6.27 (m, 1H), 5.18 (s, 2H), 2.81 (t, J=7.5 Hz, 2H), 2.70 (m, 4H), 2.61 (m, J=7.0 Hz, 2H), 1.98 (m, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2dfa06d3ee794d4e85d3d85b5e59d595
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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