Trifluoroacetic acid → 1-(3-(4-Octylphenoxy)-2-oxopropyl)indole-5-carboxylic acid

HRID 1821948Notes

Reaction equation

HRID 1821948 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][C:18](=[O:35])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:22]=1)[CH:12]=[CH:11]2)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:18](=[O:35])[CH2:17][N:13]2[C:14]3[C:10](=[CH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:16][CH:15]=3)[CH:11]=[CH:12]2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12992907tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylate

Product 1

HCID 116903251-(3-(4-Octylphenoxy)-2-oxopropyl)indole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.222 g (0.465 mmol) tert-butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylate is dissolved in 60 ml absolute dichloromethane and mixed with 3.98 g (34.9 mmol) trifluoroacetic acid. Having stirred at room temperature for 4 hours, concentration to dryness is carried out on the rotary evaporator. Two admixtures with hexane and respective concentration to dryness on the rotary evaporator leave as a crude product a brownish solid which is purified on an RP-HPLC column by means of chromatography (stationary phase: cromasil, mobile phase acetonitrile/water 80:20) and yields the product as a white solid.

Workup

  1. concentrationconcentration to dryness
  2. customis carried out on the rotary evaporator
  3. concentrationTwo admixtures with hexane and respective concentration to dryness
  4. customon the rotary evaporator
  5. customleave as a crude product a brownish solid which
  6. customis purified on an RP-HPLC column by means of chromatography (stationary phase: cromasil, mobile phase acetonitrile/water 80:20)

Sources & evidence

ORD record
ord-c1933ac4abbb4c778c87c8ed5fad0b8e
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…