Trifluoroacetic acid → 5-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 49057Notes

Reaction equation

HRID 49057 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 695871365-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 695870585-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-tert-butoxycarbonyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester (1.6 g, 5 mmol) in dichloromethane (12 mL) was added 8 mL of 40% trifluoroacetic acid. The mixture was stirred at room temperature for 1 hour. The reaction was concentrated, dissolved in toluene, concentrate, dissolved in dichloromethane and concentrated to give 1.3 g (99%) of 5-(2-carboxy-ethyl)-1H-indole-2-carboxylic acid ethyl ester.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in toluene
  3. concentrationconcentrate
  4. dissolutiondissolved in dichloromethane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a024ee04a7648faa5b7842d003dff3f
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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