Lithium Hydroxide → HCID 57887237, compound

HRID 1819687Notes

Reaction equation

HRID 1819687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:17])[NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:5]2[CH2:18][C:19]([O:21]C)=[O:20].[Li+].[OH-].CCOC(C)=O>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:17])[NH:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[C:5]2[CH2:18][C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 69057413methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetate

Product 1

HCID 57887237HCID 57887237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step I (2): To a solution of methyl 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetate (80 mg, 0.22 mmol) in THF (2.0 mL) was added a solution of LiOH (16 mg, 0.66 mmol) in water (0.5 mL). The mixture was stirred at rt for 3 h. 100 mL of EtOAc was added, and the resulting solution was washed with 0.1 N HCl and water. The organic layer was dried over Na2SO4, and the solvents was removed to give the title compound 2-(5-bromo-2-(tert-butylcarbamoyl)-1H-indol-3-yl)acetic acid which was used without further purification. MS (ESI) (M+H)+=355.03.

Workup

  1. washthe resulting solution was washed with 0.1 N HCl and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvents was removed

Sources & evidence

ORD record
ord-4c593756518a4decaf33808d5413ef23
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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