Hydrochloric Acid → [Rac]-2-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionic acid

HRID 479159Notes

Reaction equation

HRID 479159 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([O:31][CH2:32][CH3:33])[CH2:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)C.[Li+].[OH-].Cl>O1CCOCC1.O>[CH2:32]([O:31][CH:5]([CH2:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:22][C:23]=2[CH3:24])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)[C:4]([OH:34])=[O:3])[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69557258[Rac]-2-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionic acid ethyl ester

Product 1

HCID 18003605[Rac]-2-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionic acidYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

[rac]-2-Ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionic acid ethyl ester (850 mg, 1.83 mmol ) was dissolved in 10 ml of dioxane; 5 ml of water and LiOH (4.58 ml of a 1N solution in water, 4.58 mmol) were then added slowly 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 AcOEt. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a colorless solid that was triturated in CH3CN for 15 minutes, filtered and dried to yield 470 mg (58.9%) of [rac]-2-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionic acid as colorless crystals.

Workup

  1. additionpoured onto ice
  2. extractionextracted 3 times with AcOEt
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a colorless solid
  7. customthat was triturated in CH3CN for 15 minutes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-40ac34000a644552976bc6d1b7c469e3
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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