Methanesulfonate → 3-(4-[[3-Chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazol-4-yl]methoxy]-2-(trifluoromethyl)phenyl)propanoic acid

HRID 2177406Notes

Reaction equation

HRID 2177406 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([CH:9]2[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH2:10]2)[S:4][N:3]=1.S([O-])(=O)(=O)C.O[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:24]([C:35]([F:38])([F:37])[F:36])[CH:23]=1>>[Cl:1][C:2]1[C:6]([CH2:7][O:8][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([C:35]([F:36])([F:38])[F:37])[CH:23]=2)=[C:5]([C:9]2[CH2:14][CH2:13][CH:12]([CH3:15])[CH2:11][CH:10]=2)[S:4][N:3]=1

Participants

4

Reactant 3

HCID 85257MethanesulfonateHCID 587538593-(4-Hydroxy-2-trifluoromethyl-phenyl)-propionic acid ethyl esterHCID 118184942(3-Chloro-5-(4-methylcyclohex-3-en-1-yl)isothiazol-4-yl)methanol

Product 1

HCID 1181849163-(4-[[3-Chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazol-4-yl]methoxy]-2-(trifluoromethyl)phenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 127, following Steps 6-7, by conversion of (3-chloro-5-(4-methylcyclohex-3-en-1-yl)isothiazol-4-yl)methanol to the corresponding mesylate and coupling with ethyl 3-(4-hydroxy-2-trifluoromethylphenyl)propanoate. Upon hydrolysis, compound 276 was afforded as an off-white solid. 1H NMR (300 MHz, CD3OD) δ: 7.24-7.30 (m, 1H), 7.10-7.23 (m, 1H), 7.06-7.10 (m, 1H), 6.13 (bs, 1H), 4.96 (s, 2H), 3.11 (t, J=7.6 Hz, 2H), 2.68 (t, J=7.6 Hz, 2H), 2.42-2.65 (m, 3H), 1.71-1.87 (m, 3H), 1.26-1.42 (m, 1H), 0.99 (d, J=6.3 Hz, 3H). 19F NMR (300 MHz, CD3OD) δ: −60.07. Mass spectrum (ESI, m/z): Calcd. for C21H21ClF3NO3S, 458.1 (M−H). found 458.2.

Workup

  1. customThe title compound was prepared
  2. customUpon hydrolysis

Sources & evidence

ORD record
ord-f1f8de087dc0436cbb4e5951880fdde7
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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