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

HRID 2177346Notes

Reaction equation

HRID 2177346 reaction equation
C(C1C=CC(C2C=C(C)SC=2CO)=CC=1)C.OC1C(F)=CC(CCC(OCC)=O)=CC=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[C:54]([F:55])=[CH:53][C:52]([CH2:56][CH2:57][C:58]([O:60]CC)=[O:59])=[CH:51][C:50]=2[F:63])=[CH:37][CH:36]=1)[CH3:34]>>[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[C:50]([F:63])=[CH:51][C:52]([CH2:56][CH2:57][C:58]([OH:60])=[O:59])=[CH:53][C:54]=2[F:55])=[CH:37][CH:36]=1)[CH3:34]

Participants

4

Reactant 3

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418314(3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methanolHCID 90418817Ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoate

Product 1

HCID 854733633-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 196 step 7 by coupling of (3-(4-ethylphenyl)-5-methylthiophen-2-yl)methanol and ethyl 3-(4-hydroxy-3,5-difluoro phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=7.0 Hz, 2H), 7.21 (d, J=7.1 Hz, 2H), 6.88 (s, 1H), 6.75 (d, J=7.8 Hz, 2H), 5.10 (s, 2H), 2.85 (t, J=7.5 Hz, 2H), 2.65 (t, J=7.0 Hz, 2H), 2.45 (s, 3H), 2.01 (m, J=7.8 Hz, 2H), 1.25 (t, J=7.2 Hz, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a4a7cfb9df3b423486442a76af294edd
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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