Trifluoroacetic acid → 5-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester

HRID 49048Notes

Reaction equation

HRID 49048 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]([O: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]([O: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 695874395-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 695866655-carboxymethoxy-1H-indole-2-carboxylic acid ethyl esterYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-tert-butoxycarbonylmethoxy-1H-indole-2-carboxylic acid ethyl ester (2 g, 6 mmol) and trifluoroacetic acid (8 mL) in dichloromethane (8 mL) was stirred at room temperature for 2 hours. The reaction was concentrated to give 1.6 g (97%) of 5-carboxymethoxy-1H-indole-2-carboxylic acid ethyl ester as a light brown solid.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-97e0e3d6a9364f4f8edc82a1239805fa
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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