Trifluoroacetic acid → HCID 68682899, compound

HRID 1820486Notes

Reaction equation

HRID 1820486 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][C@H:21]3[CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:19])=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:31]([N:33]1[CH2:38][CH2:37][C:36]([F:40])([F:39])[CH2:35][CH2:34]1)=[O:32])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:40][C:36]1([F:39])[CH2:37][CH2:38][N:33]([C:31]([C:10]2[N:9]([CH2:8][CH2:7][OH:6])[C:17]3[C:12]([CH:11]=2)=[CH:13][C:14]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:19])=[CH:15][CH:16]=3)=[O:32])[CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68681279HCID 68681279, compound

Product 1

HCID 68682899HCID 68682899, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 90 mg (0.15 mmol) [1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanone in 3 mL dichloromethane was cooled to 0° C. and 1.0 mL (1.49 g, 13.1 mmol) trifluoroacetic acid were added. The cooling bath was removed and after stirring for 1 h at room temperature the pH of the solution was neutralized by adding 1M aqueous sodium hydroxide solution. The phases were separated and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol as eluant (gradient 100:0 to 50:50) to give 41 mg (56%) of the desired compound as a white foam.

Workup

  1. customThe cooling bath was removed
  2. additionby adding 1M aqueous sodium hydroxide solution
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted three times with dichloromethane
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash column chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-b4dff62702564a62945b6c1bd5addd17
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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