Trifluoroacetic acid → HCID 68429255, compound

HRID 2092101Notes

Reaction equation

HRID 2092101 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:26][C@@H:27]1[CH2:32][C@@H:31]2[CH2:33][C@@H:29]([C:30]2([CH3:35])[CH3:34])[C@H:28]1[CH3:36].FC(F)(F)C(O)=O.C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C@H:14]2[CH2:18][CH2:17][NH:16][CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:26][C@@H:27]1[CH2:32][C@@H:31]2[CH2:33][C@@H:29]([C:30]2([CH3:35])[CH3:34])[C@H:28]1[CH3:36]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 86647512HCID 86647512, compound

Product 1

HCID 68429255HCID 68429255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl (3S)-3-[({[5-bromo-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]acetyl}amino)methyl]pyrrolidine-1-carboxylate (72.5 mg, 0.13 mmol) in dichloromethane (2 mL) was mixed with trifluoroacetic acid (19.7 μL, 0.26 mmol) at room temperature and stirred at room temperature for 12 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1) to give the desired product.

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-f553f9242c8f4093927facb4b3a2fbb1
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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