Sodium Hydroxide → HCID 89740157, compound

HRID 2206523Notes

Reaction equation

HRID 2206523 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[N:5]([CH:17]([CH3:25])[C:18](=[O:24])[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:6]2[C:11]([C:12]=1[C:13]([O:15]C)=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2>O1CCCC1.C1(C)CCC(C(C)C)C(O)C1.O>[CH3:3][C:4]1[N:5]([CH:17]([CH3:25])[C:18](=[O:24])[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[C:6]2[C:11]([C:12]=1[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 117778625HCID 117778625, compound

Product 1

HCID 89740157HCID 89740157, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1254MentholSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of sodium hydroxide solution (50 mg, 1.2 mmol) in tetrahydrofuran, menthol and water (20 mL, 3:1:1, V/V) was added methyl 2-methyl-1-(1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.318 mmol). The reaction mixture was stirred at 70° C. for 10 hours. The mixture was quench with 10% hydrochloric acid aqueous (2 mL), extracted with dichloromethane and menthol (60 mL, 10:1). The combine organic layer was dried by anhydrous sodium sulfate, filtered and concentrated to give 2-methyl-1-(1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-1H-indole-3-carboxylic acid (90 mg, 92%). LCMS (M+H+) m/z: calcd 300.15. found 300.

Workup

  1. customThe mixture was quench with 10% hydrochloric acid aqueous (2 mL)
  2. extractionextracted with dichloromethane and menthol (60 mL, 10:1)
  3. dry with materialThe combine organic layer was dried by anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5479a7d1794b4789a84aea0c30763c68
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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