Hydrochloric Acid → Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid

HRID 11383Notes

Reaction equation

HRID 11383 reaction equation
C([O:3][C:4](=[O:36])[CH:5]([O:33][CH2:34][CH3:35])[CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[CH2:16][C:17]1[N:18]=[C:19]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[CH:24]=2)[O:20][C:21]=1[CH3:22])C.[Li+].[OH-].Cl>O1CCOCC1>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([C:19]2[O:20][C:21]([CH3:22])=[C:17]([CH2:16][N:11]3[C:12]4[C:8](=[C:7]([CH2:6][CH:5]([O:33][CH2:34][CH3:35])[C:4]([OH:36])=[O:3])[CH:15]=[CH:14][CH:13]=4)[CH:9]=[CH:10]3)[N:18]=2)[CH:24]=[C:25]([O:31][CH3:32])[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69279866Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acid ethyl ester

Product 1

HCID 10434588Rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-4-yl}-2-ethoxy-propionic acidYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

rac-3-{1-[2-(3,5-Dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-4-yl}-2-ethoxy-propionic acid ethyl ester (0.390 g, 0.79 mmol ) was dissolved in 15 ml of dioxane; 1.98 ml of an aqueous solution of LiOH (1.0 molar, 1.98 mmol) were then added at room temperature. The resulting mixture was stirred overnight at room temperature and then poured onto ice, neutralized to pH 4 with HCl (1N) and extracted 3 times with MeCl2. The combined organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 0.242 g (66 %) of rac-3-{1-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-4-yl}-2-ethoxy-propionic acid as light yellow solid.

Workup

  1. additionpoured onto ice
  2. extractionextracted 3 times with MeCl2
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0399fb9c8f3b4bd0ae21245113911683
Source dataset
uspto-grants-2006_08
Patent number
US07098228B2

Reaction notes

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