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

HRID 1821944Notes

Reaction equation

HRID 1821944 reaction equation
C([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][C:18](=[O:35])[CH2:19][O:20][C:21]2[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]=2)[CH:9]=1)=[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:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:6]([OH:7])=[O:5])=[CH:9]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 12992905tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3-carboxylate

Product 1

HCID 115535641-[3-(4-Octylphenoxy)-2-oxopropyl]indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.072 g (0.151 mmol) tert-butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-3-carboxylate is dissolved in 10 ml absolute dichloromethane and mixed with 1.56 g (13.7 mmol) trifluoroacetic acid. Having stirred at room temperature for 1 hour, concentration to dryness is carried out on the rotary evaporator. Two dissolution steps in toluene and respective concentration on the rotary evaporator leave as the crude product a reddish solid which is recrystallized from petroleum ether/ethyl acetate (67:33) and yields the product as a white solid.

Workup

  1. concentrationconcentration to dryness
  2. customis carried out on the rotary evaporator
  3. dissolutionTwo dissolution steps in toluene
  4. concentrationrespective concentration
  5. customon the rotary evaporator
  6. customleave as the crude product a reddish solid which
  7. customis recrystallized from petroleum ether/ethyl acetate (67:33)

Sources & evidence

ORD record
ord-1b47f9f857924ee5acc70a28059af9a0
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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