Lithium Hydroxide → [rac]-Lithium 2-ethoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4yl)-ethoxy]-phenyl}-propionate

HRID 479189Notes

Reaction equation

HRID 479189 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:30][CH2:31][CH3:32])[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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:9]([O:28][CH3:29])[CH:8]=1)C.[OH-].[Li+:35]>O1CCOCC1.O>[CH2:31]([O:30][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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:9]([O:28][CH3:29])[CH:8]=1)[C:4]([O-:33])=[O:3])[CH3:32].[Li+:35]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69556647[rac]-2-Ethoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4yl)-ethoxy]-phenyl}-propionic acid ethyl ester

Product 1

HCID 131724206[rac]-Lithium 2-ethoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4yl)-ethoxy]-phenyl}-propionateYield 43.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

[rac]-2-Ethoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4yl)-ethoxy]-phenyl}-propionic acid ethyl ester (306 mg, 0.67 mmol) were dissolved in 3 ml dioxane and 2 ml water, 50 mg lithium hydroxide were added and the mixture stirred at r.t. during 24 hours. The reaction mixture was then chromatographed (MCI-gel; CH3CN/H2O) as lithium salt to yield 125 mg (43%) of the title compound as a white gum.

Workup

  1. customThe reaction mixture was then chromatographed (MCI-gel; CH3CN/H2O) as lithium salt

Sources & evidence

ORD record
ord-71ca2afb7bd4493083dc82835d1b1ec8
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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