Lithium Hydroxide → HCID 23510277, compound

HRID 1883115Notes

Reaction equation

HRID 1883115 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([O:19]CC)=[O:18])[NH:14]2)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3].[OH-].[Li+]>CO.O>[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]([OH:19])=[O:18])[NH:14]2)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23510061HCID 23510061, compound

Product 1

HCID 23510277HCID 23510277, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 134 mg (0.465 mmol) of ethyl 6{[(allyloxy)carbonyl]amino}-1H-indole-2-carboxylate dissolved in 5 mL methanol was added 43 mg (1.023 mmol) lithium hydroxide dissolved in 1 mL water. The mixture was stirred at room temperature overnight, partitioned between ethyl acetate and 1 N HCl until neutral, dried over magnesium sulfate and concentrated to provide 118 mg 6-{[(allyloxy)carbonyl]amino}-1H-indole-2-carboxylic acid, as a colorless solid.

Workup

  1. custompartitioned between ethyl acetate and 1 N HCl until neutral,
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-50b386ac03334b6cad6efafd928b2411
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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