Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate → 3-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-difluorophenyl)propanoic acid

HRID 2177348Notes

Reaction equation

HRID 2177348 reaction equation
C(C1C=CC(C2C=C(C)SC=2CO)=CC=1)C.OC1C=CC(CCC(OCC)=O)=C(F)C=1F.[CH2:33]([C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:45]=[C:44]([CH3:46])[S:43][C:42]=2[CH2:47][O:48][C:49]2[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][C:57]([O:59]CC)=[O:58])=[C:51]([F:62])[C:50]=2[F:63])=[CH:37][CH:36]=1)[CH3:34]>>[CH2:33]([C:35]1[CH:36]=[CH:37][C:38]([C:41]2[CH:45]=[C:44]([CH3:46])[S:43][C:42]=2[CH2:47][O:48][C:49]2[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][C:57]([OH:59])=[O:58])=[C:51]([F:62])[C:50]=2[F:63])=[CH:39][CH:40]=1)[CH3:34]

Participants

4

Reactant 3

HCID 90404786Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoateHCID 90418157Ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-difluorophenyl)propanoateHCID 90418314(3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methanol

Product 1

HCID 854733643-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-difluorophenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 208 by coupling of (3-(4-ethylphenyl)-5-methylthiophen-2-yl)methanol and ethyl 3-(4-hydroxy-2,3-difluoro phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=7.9 Hz, 2H), 7.30 (s, 1H), 7.25 (d, J=7.5 Hz, 2H), 7.02 (d, J=7.8 Hz, 1H), 6.68 (d, J=7.5 Hz, 1H), 5.10 (s, 2H), 2.98 (t, J=7.5 Hz, 2H), 2.71 (m, J=7.8 Hz, 2H), 2.68 (t, J=6.5 Hz, 2H), 2.55 (s, 3H), 1.36 (t, J=8.5 Hz, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-326fb2980ae847b88f41da41c4b37cd9
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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