Trifluoroacetic acid → Ethyl 3-phenyl-3-(6-carboxymethoxyindol-3-yl)propionate trifluoroacetate

HRID 351931Notes

Reaction equation

HRID 351931 reaction equation
[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>ClCCl>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22714448Ethyl 3-phenyl-3-[6-(tert-butoxycarbonylmethoxy)indol-3-yl]propionate

Product 1

HCID 22714548Ethyl 3-phenyl-3-(6-carboxymethoxyindol-3-yl)propionate trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (2.36 mmol) of 18 are dissolved in 20 ml of dichloromethane and stirred at room temperature for 20 hours with 2 ml of trifluoroacetic acid. The solution is subsequently evaporated, and the residue is purified by preparative HPLC on RP-18, giving ethyl 3-phenyl-3-(6-carboxymethoxyindol-3-yl)-propionate trifluoroacetate.

Workup

  1. customThe solution is subsequently evaporated
  2. customthe residue is purified by preparative HPLC on RP-18

Sources & evidence

ORD record
ord-6f1e819255f14c5db31ddb66cb5e3856
Source dataset
uspto-grants-2004_06
Patent number
US06743810B2

Reaction notes

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