Lithium Hydroxide → HCID 67106775, compound

HRID 450106Notes

Reaction equation

HRID 450106 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:32])[C:15](=[O:31])[C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[CH:18][C:17]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:8]=1)C.[OH-].[Li+]>CO.O>[O:31]=[C:15]([C:16]1[N:24]2[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]2)=[CH:18][C:17]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[O:6][CH2:5][C:4]([OH:33])=[O:3])=[O:32]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67107359HCID 67107359, compound

Product 1

HCID 67106775HCID 67106775, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of {3-[2-Oxo-2-(2-phenyl-indolizin-3-yl)-acetylamino]-phenoxy}-acetic acid ethyl ester (0.4 g, 0.90 mmol) in methanol (3 ml) was added lithium hydroxide (38 mg, 1.8 mmol) and a few drops of water. The reaction mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure. The reaction mixture was diluted with water (10 ml) and adjusted to pH 3 with 2N hydrochloric acid. The product was extracted with ether and the organic layer dried over sodium sulphate, filtered, then evaporated to dryness to yield {3-[2-oxo-2-(2-phenyl-indolizin-3-yl)-acetylamino]-phenoxy}-acetic acid (0.2 g, 53%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe reaction mixture was diluted with water (10 ml)
  3. extractionThe product was extracted with ether
  4. dry with materialthe organic layer dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f62a88f4bfca40d4a1b6f2cbde414f21
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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