Trifluoroacetic acid → HCID 178502668, compound

HRID 480379Notes

Reaction equation

HRID 480379 reaction equation
[CH3:1][O:2][N:3]([CH3:31])[C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12](C(OC(C)(C)C)=O)[C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[CH:7][CH:6]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][N:3]([CH3:31])[C:4](=[O:30])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:15][CH2:14]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178502669HCID 178502669, compound

Product 1

HCID 178502668HCID 178502668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Methoxy-N-methyl-trans-4-{[tert-butoxycarbonyl-(4-tert-butylcyclohexyl)amino]methyl}benzamide (1.0 g, 2.3 mmol) was dissolved in DCM (10 ml), and TFA (10 ml) was added. The reaction mixture was stirred at ambient temperature for 2 hours and then taken to dryness by rotary evaporation. The crystal-line residue was then dissolved in ethyl acetate (100 ml), and the organic phase was washed with saturated aqueous sodium carbonate solution (2×100 ml). The combined water phases were back extracted once with ethyl acetate (100 ml); and the combined organic phases dried with anhydrous sodium sulphate. Solvent was removed by rotary evaporation, to leave the title product as fine white crystals. Yield: 760 mg (99%).

Workup

  1. customtaken to dryness by rotary evaporation
  2. dissolutionThe crystal-line residue was then dissolved in ethyl acetate (100 ml)
  3. washthe organic phase was washed with saturated aqueous sodium carbonate solution (2×100 ml)
  4. extractionThe combined water phases were back extracted once with ethyl acetate (100 ml)
  5. dry with materialand the combined organic phases dried with anhydrous sodium sulphate
  6. customSolvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-4b6b740607294a6e8585e669c5b49fa5
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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