Sulfuric Acid → 1-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester

HRID 342808Notes

Reaction equation

HRID 342808 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])OCC[O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].S(=O)(=O)(O)O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16](=[O:17])[CH3:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 675985121-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

Product 1

HCID 675993131-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl EsterYield 59.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of crude 1-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester (2.85 g, ≈5 mmol) in acetone (60 ml) was added concentrated sulfuric acid (0.6 ml). The solution was stirred at room temperature for about 45 minutes, and most of the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (silica, 130 g) eluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane, to give the title compound (1.48 g).

Workup

  1. custommost of the solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica, 130 g)
  6. washeluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8f2bc46890764eacaba2817c227374ca
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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