Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → 3-(4-[[3-Chloro-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoic acid

HRID 2177272Notes

Reaction equation

HRID 2177272 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7]Cl)=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:4][N:3]=1.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:20]([CH3:31])[C:19]=1[CH3:32]>>[Cl:1][C:2]1[C:6]([CH2:7][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH3:31])[C:19]=2[CH3:32])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[S:4][N:3]=1

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 904183203-Chloro-4-(chloromethyl)-5-(4-methoxyphenyl)-1,2-thiazole

Product 1

HCID 904183253-(4-[[3-Chloro-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 127 following Step 6 and 7 by coupling of 3-chloro-4-(chloromethyl)-5-(4-methoxyphenyl)-1,2-thiazole 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: 7.502 (d, J=6.6 Hz, 2H), 7.00 (t, J=6.0 Hz, 3H), 6.784 (d, J=6.0 Hz, 1H), 4.925 (s, 2H), 3.87 (s, 3H), 2.99 (t, J=6.0 Hz, 2H), 2.64 (t, J=6.0 Hz, 2H), 2.27 (s, 3H), 2.18 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H22ClNO4S, 430.1 (M−H). found 430.1.

Workup

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

Sources & evidence

ORD record
ord-ec292e300ed84ec9a10ff9c983e81a9a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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