Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 90418545, compound

HRID 2177186Notes

Reaction equation

HRID 2177186 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([CH2:12][OH:13])=[C:10]([C:14]([F:17])([F:16])[F:15])[S:9][N:8]=2)[CH2:3]1.[F:19][C:20]1[CH:21]=[C:22]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH:23]=[C:24]([F:27])[C:25]=1O>>[F:18][C:2]1([F:1])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([CH2:12][O:13][C:25]3[C:24]([F:27])=[CH:23][C:22]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:21][C:20]=3[F:19])=[C:10]([C:14]([F:16])([F:17])[F:15])[S:9][N:8]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90418236HCID 90418236, compound

Product 1

HCID 90418545HCID 90418545, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling [3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol and ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 6.90-6.98 (m, 2H), 5.22 (s, 2H), 3.88-3.94 (m, 1H), 2.89 (t, J=7.5 Hz, 2H), 2.50-2.64 (m, 4H), 2.20-2.41 (m, 4H). 19F NMR (300 MHz, CD3OD) δ−56.37, −90.10, −90.91, −130.13. Mass spectrum (ESI, m/z): Calcd. for C19H16F7NO3S, 470.1 (M−H). found 470.1.

Workup

  1. customThe title compound was prepared
  2. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-493274a38b2e4aebb387299defbf9b6d
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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