Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate → HCID 85471823, compound

HRID 2177351Notes

Reaction equation

HRID 2177351 reaction equation
C(C1C=CC(C2SC=CC=2CO)=CC=1)C.OC1C=CC(CCC(OCC)=O)=C(F)C=1F.[CH2:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[CH2:45][O:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][C:55]([O:57]CC)=[O:56])=[C:49]([F:60])[C:48]=2[F:61])=[CH:36][CH:35]=1)[CH3:33]>>[CH2:32]([C:34]1[CH:35]=[CH:36][C:37]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[CH2:45][O:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][C:55]([OH:57])=[O:56])=[C:49]([F:60])[C:48]=2[F:61])=[CH:38][CH:39]=1)[CH3:33]

Participants

4

Reactant 3

HCID 90404786Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoateHCID 90418562HCID 90418562, compoundHCID 90418719HCID 90418719, compound

Product 1

HCID 85471823HCID 85471823, compound

Procedure

The title compound was prepared according to the procedure described in Example 208 by coupling of (2-(4-ethylphenyl)thiophen-3-yl)methanol and ethyl 3-(4-hydroxy-2,3-difluoro phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((2-(4-ethylphenyl)thiophen-3-yl)methoxy)-2,3-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.40 (d, J=7.1 Hz, 2H), 7.25 (m, 4H), 6.82 (t, J=6.5 Hz, 1H), 6.66 (t, J=6.5 Hz, 1H), 5.10 (s, 2H), 2.95 (t, J=7.5 Hz, 2H), 2.65 (t, J=7.0 Hz, 2H), 1.31 (t, J=9.5 Hz, 3H). LCMS (ESI, M/Z) for C22H20F2O3S: 403.1 (MH+).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-be8251378e5043c4aa562d79ce3df4c8
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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