Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418276, compound

HRID 2177192Notes

Reaction equation

HRID 2177192 reaction equation
[F:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([CH2:15][OH:16])=[C:13]([C:17]([F:20])([F:19])[F:18])[S:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].O[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:24]([CH3:35])[C:23]=1[CH3:36]>>[F:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([CH2:15][O:16][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([CH3:35])[C:23]=3[CH3:36])=[C:13]([C:17]([F:20])([F:19])[F:18])[S:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3]

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418302HCID 90418302, compound

Product 1

HCID 90418276HCID 90418276, 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-fluoroethyl)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. 1HNMR (300 MHz, CD3OD) δ 7.67 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 6.92 (d, J=8.1 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H), 5.53-5.75 (m, 1H), 5.06 (s, 2H), 2.89 (t, J=7.5 Hz, 2H), 2.47 (t, J=7.5 Hz, 2H), 2.18 (s, 3H), 2.00 (s, 3H), 1.53-1.65 (m, 3H). Mass spectrum (ESI, m/z): Calcd. for C24H23F4NO3S, 480.1 (M−H). found 480.1.

Workup

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

Sources & evidence

ORD record
ord-c1fea5390c414c63bf27f48a2a53eb01
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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