Trifluoroacetic acid → HCID 22614947, compound

HRID 843174Notes

Reaction equation

HRID 843174 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[N:14]([CH2:22][CH2:23][CH2:24][O:25][C:26]1[C:31]2[C:32]([CH3:43])=[C:33]([CH:35]=[CH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:34][C:30]=2[CH:29]=[CH:28][CH:27]=1)[CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(C)(C)C.ClCCl>ClCCl>[CH3:43][C:32]1[C:31]2[C:26]([O:25][CH2:24][CH2:23][CH2:22][NH:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:27][CH:28]=[CH:29][C:30]=2[O:34][C:33]=1/[CH:35]=[CH:36]/[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757975HCID 86757975, compound

Product 1

HCID 22614947HCID 22614947, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10% trifluoroacetic acid in dichloromethane [3-(3-methyl-2-styryl-benzofuran-4-yloxy)-propyl]-pyridin-3-ylmethyl-carbamic acid tert-butyl ester (15 mg) in dichloromethane (1 ml) was added with ice-cooling. After 3 hours, the mixture was quenched with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (dichloromethane-MeOH) to give a colorless solid (7 mg, 58%). ESI-MS: m/z 399 (MH+); 1H-NMR (CDCl3): δ 2.12 (2H, s), 2.37 (3H, s), 2.94 (2H, t, J=6.9 Hz), 3.91 (2H, s), 4.14 (2H, t, J=5.9 Hz), 6.57 (1H, d, J=7.6 Hz), 7.02-7.28 (5H, m), 7.37 (2H, t, J=7.6 Hz), 7.53 (2H, d, J=7.6 Hz), 7.73 (2H, d, J=7.9 Hz), 8.52 (1H, d, J=4.6 Hz), 8.61 (1H, s).

Workup

  1. temperaturecooling
  2. customthe mixture was quenched with saturated sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (dichloromethane-MeOH)

Sources & evidence

ORD record
ord-26536eeee70b4ce08f2f53200c936dce
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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