Lithium Hydroxide → 2-Ethoxy-3-(2-methyl-4-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-propionic acid

HRID 394377Notes

Reaction equation

C([O:3][C:4](=[O:38])[CH:5]([O:35][CH2:36][CH3:37])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[CH3:33])[CH:15]([CH3:17])[CH3:16])=[CH:9][C:8]=1[CH3:34])C.[Li+].[OH-]>>[CH2:36]([O:35][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]([C:18]2[S:22][C:21]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=3)=[N:20][C:19]=2[CH3:33])[CH:15]([CH3:16])[CH3:17])=[CH:9][C:8]=1[CH3:34])[C:4]([OH:38])=[O:3])[CH3:37]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 686171842-Ethoxy-3-(2-methyl-4-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-propionic acid ethyl ester

Product 1

HCID 226474692-Ethoxy-3-(2-methyl-4-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-propionic acid

Procedure

In analogy to the procedure described in example 10 d], 2-ethoxy-3-(2-methyl-4-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-propionic acid ethyl ester (mixture of two diastereomeric racemates) was treated with LiOH to obtain 2-ethoxy-3-{2-methyl-4-(2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-phenyl)-propionic acid as a mixture of two diastereomeric racemates as colorless foam.

Workup

customdescribed in example 10 d

Sources & evidence

ORD record: ord-b53e9a0d0bae40cda6b78daf82e42bf5
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Reaction notes

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