Trifluoroacetic acid → HCID 66810863, compound

HRID 2356774Notes

Reaction equation

HRID 2356774 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][C:23]([C:25]3[C:33]4[N:32]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[NH:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([CH2:21][NH:22][C:23]([C:25]3[C:33]4[N:32]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[NH:30][C:29]=4[CH:28]=[CH:27][CH:26]=3)=[O:24])[CH2:19][CH2:20]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66810908HCID 66810908, compound

Product 1

HCID 66810863HCID 66810863, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 4-(4-{[(2-tert-butyl-1H-benzoimidazole-4-carbonyl)amino]methyl}-piperidin-1-ylmethyl)piperidine-1-carboxylic acid tert-butyl ester, prepared as in the previous step (5.1 g, 10 mmol) was treated with a mixture of trifluoroacetic acid (40 mL) and dichloromethane (40 mL) at room temperature for 0.5 h. The mixture was concentrated in vacuo, redissolved in dichloromethane (25 mL) and basified with 1M aqueous sodium hydroxide (15 mL). The organic layer was removed, and the aqueous layer re-extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product as a brown foam (3.6 g, 8.8 mmol, 88%). (m/z): [M+H]+ calcd for C24H37N5O 412.31, found 412.6.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved in dichloromethane (25 mL)
  3. customThe organic layer was removed
  4. extractionthe aqueous layer re-extracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0797d02b337487a84f2701f3d4dbf76
Source dataset
uspto-grants-2010_07
Patent number
US07759363B2

Reaction notes

Loading…