Lithium Hydroxide → HCID 10021863, compound

HRID 2083920Notes

Reaction equation

HRID 2083920 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][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])=[CH:9][C:8]=1[OH:28])C.[Li+].[OH-]>O1CCCC1>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C:4]([OH:29])=[O:3])=[C:8]([OH:28])[CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10475786HCID 10475786, compound

Product 1

HCID 10021863HCID 10021863, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{2-Hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester (60 mg, 0.15 mmol) was dissolved in tetrahydrofuran (5 mL) and treated with LiOH (1 mL, 1M). After stirring 18 hours at ambient temperature, the reaction was evaporated and partitioned between NH4Cl (sat.) and ethyl acetate. Extraction with ethyl acetate, followed by drying over anhydrous Na2SO4, and evaporation of solvent provided 27.1 mg of the title compound. MS m/z 368 (M+H)+.

Workup

  1. customthe reaction was evaporated
  2. custompartitioned between NH4Cl (sat.) and ethyl acetate
  3. extractionExtraction with ethyl acetate
  4. dry with materialby drying over anhydrous Na2SO4, and evaporation of solvent

Sources & evidence

ORD record
ord-fdc4b544b52243cfbdab375ab6d8b70f
Source dataset
uspto-grants-2004_04
Patent number
US06716842B2

Reaction notes

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