Trifluoroacetic acid → HCID 71618475, compound

HRID 64469Notes

Reaction equation

HRID 64469 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:23][C:24]([OH:26])=[O:25])=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713494tert-butyl (3R)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylhexanoate

Product 1

HCID 71618475HCID 71618475, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 216 mg of tert-butyl (3R)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylhexanoate in 2 ml of dichloromethane was added 2 ml of trifluoroacetic acid, followed by stirring overnight. The solvent was evaporated under reduced pressure, and water, a saturated aqueous sodium hydrogen carbonate solution, 1 M hydrochloric acid, and chloroform were added thereto to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. To the obtained purified product were added ethyl acetate and diisopropyl ether, and the resulting solid was collected by filtration and dried to obtain 147 mg of (3R)-3-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}amino)-5-methylhexanoic acid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additiona saturated aqueous sodium hydrogen carbonate solution, 1 M hydrochloric acid, and chloroform were added
  3. customa layer separation operation
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography
  7. customTo the obtained purified product
  8. additionwere added ethyl acetate and diisopropyl ether
  9. filtrationthe resulting solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-c7043a3f44dc44949fc3181cf001c9be
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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