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

HRID 1821939Notes

Reaction equation

HRID 1821939 reaction equation
C([O:5][C:6]([C:8]1[N:9]([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)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[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:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[C:8]2[C:6]([OH:7])=[O:5])=[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 11670138tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-2-carboxylate

Product 1

HCID 115026871-[3-(4-Octylphenoxy)-2-oxopropyl]indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.046 g (0.096 mmol) tert-butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-2-carboxylate is dissolved in 10 ml absolute dichloromethane and mixed with 1.49 g (13.6 mmol) trifluoroacetic acid. Having stirred at room temperature for 1½ hours, concentration to dryness is carried out on the rotary evaporator. Two dissolution steps in toluene and respective concentration on the rotary evaporator leave as a crude product a yellowish 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 a crude product a yellowish solid which
  7. customis recrystallized from petroleum ether/ethyl acetate (67:33)

Sources & evidence

ORD record
ord-accb2994a88d4fd98f8b40d96f858e95
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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