Trifluoroacetic acid → HCID 11532809, compound

HRID 1821954Notes

Reaction equation

HRID 1821954 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:38])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:23][CH:22]=1)[CH:12]=[CH:11]2)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:18](=[O:38])[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:22][CH:23]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11562683HCID 11562683, compound

Product 1

HCID 11532809HCID 11532809, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.096 mmol) tert-butyl-1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-5-carboxylate are dissolved in 15 ml absolute dichloromethane and mixed with 0.82 g (7.19 mmol) trifluoroacetic acid. Having stirred at room temperature for 4 hours, the batch is concentrated to dryness on the rotary evaporator. Three admixtures with 10 ml of a mixture of petroleum ether and ethyl acetate (4:1) 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 by means of chromatography (stationary phase: cromasil, flow agent: acetonitrile/water 90:10).

Workup

  1. concentrationthe batch is concentrated to dryness on the rotary evaporator
  2. concentrationThree admixtures with 10 ml of a mixture of petroleum ether and ethyl acetate (4:1) each and respective concentration to dryness
  3. customon the rotary evaporator

Sources & evidence

ORD record
ord-ab22a6757e7b48f6bc5c5f5642d72ba1
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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