Trifluoroacetic acid → HCID 11647468, compound

HRID 1821949Notes

Reaction equation

HRID 1821949 reaction equation
C([O:5][C:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][N:14]2[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:10][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:14]2[C:15]3[C:11](=[CH:10][CH:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:16]=3)[CH:12]=[CH:13]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 68840623HCID 68840623, compound

Product 1

HCID 11647468HCID 11647468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

59 mg (0.12 mmol) tert-butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-6-carboxylate are dissolved in 15 ml absolute dichloromethane and mixed with 1.05 g (9.20 mmol) trifluoroacetic acid. After stirring at room temperature for 2½ hours, concentration to dryness is carried out on the rotary evaporator. Three admixtures with 10 ml of a mixture of petroleum ether and ethyl acetate (1:2) each and respective concentration to dryness on the rotary evaporator leave as a crude product a solid which is purified on an RP-HPLC column (stationary phase: cromasil, mobile phase: acetonitrile/water 9:1) by means of chromatography.

Workup

  1. concentrationconcentration to dryness
  2. customis carried out on the rotary evaporator
  3. concentrationThree admixtures with 10 ml of a mixture of petroleum ether and ethyl acetate (1:2) each and respective concentration to dryness
  4. customon the rotary evaporator

Sources & evidence

ORD record
ord-b5d000efe009490d884e609cc3fdff98
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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