Methanol → 5-acetamido-1H-indole-2-carboxylic Acid

HRID 1874829Notes

Reaction equation

HRID 1874829 reaction equation
[OH-].[Li+].[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(OCCC(C)(C)C)=O)[C:11]([C:25]([O-:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4].CO.O>C1COCC1>[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:25]([OH:27])=[O:26])=[CH:10]2)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 867616451-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate

Product 1

HCID 107751705-acetamido-1H-indole-2-carboxylic AcidYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (0.028 g, 1.184 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 5-(acetylamino)-1H-indole-1,2-dicarboxylate (0.041 g, 0.118 mmol) in THF:MeOH:water/3:1:1. The reaction mixture was heated at 50° C. for 1 h. The solvent was evaporated. The residue was dissolved in water, acidified with 6N aqueous HCl and extracted with dichloromethane. A solid formed in the aqueous layer which was collected by filtration and dried to give the title compound (0.011 g, 43%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.85 (s, 1H), 11.63 (s, 1H), 9.79 (s, 1H), 7.97 (s, 1H), 7.22-7.38 (m, 2H), 7.01 (s, 1H), 2.01 (s, 3H). MS: m/z 219 (M+1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. customA solid formed in the aqueous layer which
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-1c71022b3f0046cc8e2113237c7c4923
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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