Trifluoroacetic acid → HCID 10889813, compound

HRID 1786467Notes

Reaction equation

HRID 1786467 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([CH3:17])[CH:9]=2)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([CH3:17])[CH:9]=2)=[O:5])[CH3:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68565294HCID 68565294, compound

Product 1

HCID 10889813HCID 10889813, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.20 g (0.60 mmol) 5-methoxy-6-methyl-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 4 mL dichloromethane was cooled to 0° C. and 2 mL (3.0 g, 26.1 mmol) trifluoroacetic acid were added. The ice bath was removed and after stirring 1 h at room temperature the solution was evaporated to dryness. The residue was dissolved in dichloromethane, washed with aqueous 1M sodium hydroxide solution and brine, dried over magnesium sulfate, filtered and evaporated to afford the title compound as a white solid (97%) which was pure enough to be used in the next step.

Workup

  1. customThe ice bath was removed
  2. customwas evaporated to dryness
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with aqueous 1M sodium hydroxide solution and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d044932258fe475c8040a0b2971784b8
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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