Trifluoroacetic acid → HCID 70913576, compound

HRID 2208923Notes

Reaction equation

HRID 2208923 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]([CH3:41])=[C:16]([N:24]([CH2:39][CH3:40])[CH:25]2[CH2:30][CH2:29][CH:28]([NH:31]C(=O)OC(C)(C)C)[CH2:27][CH2:26]2)[CH:17]=[C:18]([O:20][CH2:21][CH2:22][OH:23])[CH:19]=1)=[O:13].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:31][CH:28]1[CH2:27][CH2:26][CH:25]([N:24]([CH2:39][CH3:40])[C:16]2[C:15]([CH3:41])=[C:14]([CH:19]=[C:18]([O:20][CH2:21][CH2:22][OH:23])[CH:17]=2)[C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:13])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86719576HCID 86719576, compound

Product 1

HCID 70913576HCID 70913576, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4-((3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-5-(2-hydroxyethoxy)-2-methylphenyl)-(ethyl)-amino)cyclohexyl)carbamate (0.80 g, 1.40 mmol) in DCM (5 mL) was added TFA (2 mL) and the reaction mixture was stirred at rt for 1 h. After completion of reaction, the solvent was removed under reduced pressure and saturated NaHCO3 solution was added. Extraction was carried out using 10% MeOH/DCM; the combined organic layers were washed with water and brine; dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure to give the title compound (0.5 g, 76%).

Workup

  1. customAfter completion of reaction
  2. customthe solvent was removed under reduced pressure and saturated NaHCO3 solution
  3. additionwas added
  4. extractionExtraction
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99c4c999db9245afb9c31e661496d8b6
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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