Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → 3-(4-[[3-(4-Ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoic acid

HRID 2177210Notes

Reaction equation

HRID 2177210 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=2)=[N:9][S:10][C:11]=1[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=O)=O.O[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[C:30]([CH3:41])[C:29]=1[CH3:42]>>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([C:8]2[C:7]([CH2:6][O:5][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[C:30]([CH3:41])[C:29]=3[CH3:42])=[C:11]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[S:10][N:9]=2)=[CH:20][CH:21]=1)[CH3:26]

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418228HCID 90418228, compound

Product 1

HCID 904175283-(4-[[3-(4-Ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 following Step 5 and 6 by coupling [3-(4-ethylphenyl)-5-(pentafluoroethyl)-1,2-thiazol-4-yl]methyl methanesulfonate and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H-NMR (300 MHz, CD3OD) δ 7.60 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.97 (d, J=8.4 Hz, 1H), 6.69 (d, J=8.4 Hz, 1H), 5.03 (s, 2H), 2.91 (t, J=8.1 Hz, 2H), 2.68 (q, J1=15.3 Hz, J2=7.5 Hz, 2H), 2.51 (t, J=8.4 Hz, 2H), 2.23 (s, 3H), 2.03 (s, 3H), 1.02 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C25H24F5NO3S, 514.1 (M+H). found 514.1.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b0950646fcc24cd5bd6cdba610e80321
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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