Trifluoroacetic anhydride → HCID 86649290, compound

HRID 2192815Notes

Reaction equation

HRID 2192815 reaction equation
[NH2:1][C:2]([C@@H:4]1[CH2:9][C@H:8]([N:10]([C:15]([C:17]2[C:18]([NH:27][CH2:28][C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[N:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[N:21][CH:22]=2)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][N:6]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:5]1)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:23]([C:20]1[N:19]=[C:18]([NH:27][CH2:28][C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[C:17]([C:15]([N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C@H:8]2[CH2:9][C@@H:4]([C:2]#[N:1])[CH2:5][N:6]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:7]2)=[O:16])=[CH:22][N:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 59625490tert-butyl (3R*,5S*)-3-(aminocarbonyl)-5-[({2-tert-butyl-4-[(2-furylmethyl)amino]pyrimidin-5-yl}carbonyl)(isobutyl)amino]piperidine-1-carboxylate

Product 1

HCID 86649290HCID 86649290, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl (3R*,5S*)-3-(aminocarbonyl)-5-[({2-tert-butyl-4-[(2-furylmethyl)amino]pyrimidin-5-yl}carbonyl)(isobutyl)amino]piperidine-1-carboxylate (469 mg) was dissolved in pyridine (5 ml), trifluoroacetic anhydride (0.25 ml) was added under ice-cooling, and the mixture was stirred at room temperature for 11 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The solution was washed successively with 1 M hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (5:95-80:20) was concentrated under reduced pressure to give the object compound (402 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe solution was washed successively with 1 M hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (5:95-80:20)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-39bc9bc889ea424c92a4873ba653291e
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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