Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418801, compound

HRID 2177194Notes

Reaction equation

HRID 2177194 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([CH2:16][OH:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[S:13][N:12]=2)=[CH:7][CH:6]=1)([F:4])[CH3:3].O[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[C:25]([CH3:36])[C:24]=1[CH3:37]>>[F:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([CH2:16][O:17][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[C:25]([CH3:36])[C:24]=3[CH3:37])=[C:14]([C:18]([F:19])([F:20])[F:21])[S:13][N:12]=2)=[CH:9][CH:10]=1)([F:1])[CH3:3]

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418686HCID 90418686, compound

Product 1

HCID 90418801HCID 90418801, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling [3-[4-(1,1-difluoroethyl)phenyl]-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 7.79 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 6.97 (d, J=8.4 Hz, 1H), 6.710 (d, J=8.4 Hz, 1H), 5.12 (s, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.52 (t, J=8.4 Hz, 2H), 2.23 (s, 3H), 2.05 (s, 3H), 1.90-2.02 (m, 3H). Mass spectrum (ESI, m/z): Calcd. for C24H22F5NO3S, 498.1 (M−H). found 498.1.

Workup

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

Sources & evidence

ORD record
ord-5bc1c06603f84a198aaad2f3386ee64b
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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