Trifluoroacetic acid → HCID 10162177, compound

HRID 2223894Notes

Reaction equation

HRID 2223894 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][C:31]([NH:33][O:34]C(C)(C)C)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][C:24]3([CH2:30][C:31]([NH:33][OH:34])=[O:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[CH2:20][CH2:21]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 10279822HCID 10279822, compound

Product 1

HCID 10162177HCID 10162177, compoundYield 31.6%

Procedure

To tert-butyl [1-[2-[4-[N-(5-methylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetohydroxamate (266 mg) was added trifluoroacetic acid (3.0 mL), and the solution was stirred at room temperature for 23 hours. The solution was then stirred at 40° C. for 2 hours and trifluoroacetic acid (2.0 mL) was further added. The solution was stirred at 50° C. for 3 hours. The trifluoroacetic acid was distilled off by azeotropic distillation with xylene. Water and chloroform were added to the residue and the solution was neutralized with saturated aqueous sodium hydrogencarbonate solution. The solution was extracted with 20% ethanol/chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, chloroform:methanol=85:15) to give the title compound (75 mg).

Workup

  1. stirringThe solution was then stirred at 40° C. for 2 hours
  2. stirringThe solution was stirred at 50° C. for 3 hours
  3. distillationThe trifluoroacetic acid was distilled off by azeotropic distillation with xylene
  4. additionWater and chloroform were added to the residue
  5. extractionThe solution was extracted with 20% ethanol/chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by chromatography (silica gel, chloroform:methanol=85:15)

Sources & evidence

ORD record
ord-3c5446dae7024ed0a191f347fb920e18
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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