Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418585, compound

HRID 2177171Notes

Reaction equation

HRID 2177171 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[C:21]([F:22])=[CH:20][C:19]([O:23][CH3:24])=[CH:18][C:17]=2[F:25])=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])=[C:29]([CH3:40])[C:28]=1[CH3:41]>>[F:25][C:17]1[CH:18]=[C:19]([O:23][CH3:24])[CH:20]=[C:21]([F:22])[C:16]=1[C:8]1[C:7]([CH2:6][O:5][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:29]([CH3:40])[C:28]=2[CH3:41])=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=1

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418709HCID 90418709, compound

Product 1

HCID 90418585HCID 90418585, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (5-(trifluoromethyl)-3-(2,6-difluoro-4-methoxyphenyl) isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 6.93 (d, J=8.4 Hz, 1H), 6.52-6.59 (m, 3H), 5.02 (s, 2H), 3.85 (s, 3H), 2.94 (t, J=7.2 Hz, 2H), 2.60 (t, J=7.5 Hz, 2H), 2.20 (s, 3H), 1.97 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C23H20F5NO4S, 502.1 (M+H). found 502.1.

Workup

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

Sources & evidence

ORD record
ord-8803fec33b0049fc89359de37bb73e65
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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