Trifluoroacetic acid → HCID 9911411, compound

HRID 1280824Notes

Reaction equation

HRID 1280824 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([NH:28][C:29]([NH2:31])=[O:30])=[C:12]([CH2:26][CH3:27])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:26]([C:12]1[N:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Br:25])[C:14]2[C:10]([C:11]=1[NH:28][C:29]([NH2:31])=[O:30])=[C:9]([O:8][CH2:7][C:6]([OH:32])=[O:5])[CH:17]=[CH:16][CH:15]=2)[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54066276HCID 54066276, compound

Product 1

HCID 9911411HCID 9911411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[[2-Ethyl-1-(2-bromo-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid tert-butyl ester (0.7 g) was dissolved in 5 mL of dichloromethane and 1 mL of trifluoroacetic acid was added. After stirring for 4 hours the reaction mixture was concentrated to dryness, the residue dissolved in ethyl acetate and extracted with 1 N sodium hydroxide. This solution was acidified and extracted with ethyl acetate, the solvent removed by flash evaporation, and the residue slurried in 1 N hydrochloric acid. The resulting greenish solid was isolated by filtration and vacuum dried. This material was flash chromatographed on silica eluting with 19:1 ethyl acetate/methanol containing 2.5% acetic acid to provide [[2-ethyl-1-(2-bromo-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid.

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionextracted with 1 N sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. customthe solvent removed by flash evaporation
  6. customThe resulting greenish solid was isolated by filtration and vacuum
  7. customdried
  8. customchromatographed on silica eluting with 19:1 ethyl acetate/methanol containing 2.5% acetic acid

Sources & evidence

ORD record
ord-39fc902ca1df476a95160ad21e4cb121
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

Loading…