Lithium Hydroxide → HCID 22273865, compound

HRID 1065007Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 69280424HCID 69280424, compound

Product 1

HCID 22273865HCID 22273865, compound

Procedure

In analogy to the procedure described in example 1 g], [rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-methyl-phenyl)-propionic acid ethyl ester was treated with LiOH to obtain [rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-methyl-phenyl)-propionic acid as colorless solid, 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-5f34da58b6cd4887b24809b973de596b
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

Loading…