Lithium Hydroxide → HCID 22273915, compound

HRID 1065003Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 69282229HCID 69282229, compound

Product 1

HCID 22273915HCID 22273915, compound

Procedure

In analogy to the procedure described in example 1 g], [rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-propionic acid ethyl ester was treated with LiOH to obtain [rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-propionic acid as colorless liquid, which can be separated into its antipodes by methods known in the art, such as separation of the antipodes via diastereomeric salts by crystallization with optically pure amines such as e.g. (R) or (S)-1-phenyl-ethylamine, (R) or (S)-1-naphthalen-1-yl-ethylamine, brucine, quinine and quinidine or by separation of the antipodes by specific chromatographic methods using either a chiral adsorbens or a chiral eluent to give the title compound.

Sources & evidence

ORD record: ord-0bb2b6a30a1949f090e6969da8f79636
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

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