Trifluoroacetic acid → ethyl 1-(2-carboxyethyl)-4-methyl-1H-indole-2-carboxylate

HRID 1600612Notes

Reaction equation

HRID 1600612 reaction equation
C([O:5][C:6]([CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[C:14]([CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[C:14]([CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15548944ethyl 1-(2-tert-butoxycarbonylethyl)-4-methyl-1H-indole-2-carboxylate

Product 1

HCID 15548945ethyl 1-(2-carboxyethyl)-4-methyl-1H-indole-2-carboxylateYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 1-(2-tert-butoxycarbonylethyl)-4-methyl-1H-indole-2-carboxylate (3.76 g, 11.4 mmol), trifluoroacetic acid (14.8 g, 130 mmol) and dichloromethane (50 ml) was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure and water was added to the residue, followed by extraction with diethyl ether (three times). The extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain ethyl 1-(2-carboxyethyl)-4-methyl-1H-indole-2-carboxylate (3.12 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with diethyl ether (three times)
  4. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-731586853b184780aeeece1a6323377c
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

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