Lithium Hydroxide → HCID 178525995, compound

HRID 2083872Notes

Reaction equation

HRID 2083872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=1)[CH:6]=[C:5]2[C:22](=[O:29])[CH:23]=[C:24]([OH:28])[C:25]([OH:27])=[O:26].[Li+].[OH-]>CO>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([C:22](=[O:29])[CH:23]=[C:24]([OH:28])[C:25]([OH:27])=[O:26])=[CH:6]2)=[CH:17][CH:16]=1)([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178497905HCID 178497905, compound

Product 1

HCID 178525995HCID 178525995, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 82 mg (0.2 mmol) of 4-[5-chloro-1-(4-methoxycarbonylbenzyl)indol-3-yl-]2-hydroxy-4-oxo-2-butenoic acid, prepared in a manner similar to that described in Example 23, in 75% MeOH (35 ml) was added 42 mg (1.0 mmol) of LiOH. After the mixture was stirred for 5 hours at room temperature, the solvent was removed under reduced pressure. The residue was acidified with 1 N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried. The solvent was evaporated and the residue was recrystallized from ethyl acetate/ether to give 63 mg of the titled compound. Yield: 79%.

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customdried
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-2458ba77af47456190bb1d43d5111c6d
Source dataset
uspto-grants-2004_04
Patent number
US06716605B2

Reaction notes

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