Lithium Hydroxide → (2S)-3-(4-{[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methoxy}-2-methylphenyl)-2-ethoxypropanoic acid

HRID 394254Notes

Reaction equation

HRID 394254 reaction equation
C[O:2][C:3](=[O:30])[C@@H:4]([O:27][CH2:28][CH3:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[S:17][CH:18]=2)=[CH:8][C:7]=1[CH3:26].[Li+].[OH-]>>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]2[S:17][CH:18]=[C:14]([CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([O:27][CH2:28][CH3:29])[C:3]([OH:30])=[O:2])=[C:7]([CH3:26])[CH:8]=3)[N:15]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 68616567(2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester

Product 1

HCID 10342734(2S)-3-(4-{[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methoxy}-2-methylphenyl)-2-ethoxypropanoic acid

Procedure

In analogy to the procedure described in example 10 d], (2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester was treated with LiOH to obtain (2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid as colorless solid, which was crystalized from hexane/AcOEt to afford colorless crystals. According to chiral HPLC of the corresponding methyl ester (Chiralcel-OJ), the enantiomeric excess amounts to 98.9%.

Workup

  1. customdescribed in example 10 d

Sources & evidence

ORD record
ord-96905cc13cc04ab489ca7d80c57ff939
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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