Trifluoroacetic acid → HCID 86648500, compound

HRID 43487Notes

Reaction equation

HRID 43487 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[C:20]([O:22]C(C)(C)C)=[O:21])[CH2:13][C@H:12]2[O:30][CH3:31])=[O:9])=[N:5][C:4]=1[C:32]([F:35])([F:34])[F:33])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([C:3]1[NH:7][C:6]([C:8]([NH:10][C@H:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[C:20]([OH:22])=[O:21])[CH2:13][C@H:12]2[O:30][CH3:31])=[O:9])=[N:5][C:4]=1[C:32]([F:34])([F:35])[F:33])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86648498tert-Butyl cis(+/-)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate

Product 1

HCID 86648500HCID 86648500, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl cis(±)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate obtained in Example (42e) (78 mg, 0.16 mmol) was dissolved in dichloromethane (3 ml). Trifluoroacetic acid (0.75 ml) was added, followed by stirring for five hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by reverse phase silica gel column chromatography (elution solvent: distilled water, acetonitrile) to obtain 60.1 mg of the title compound as a white solid (87%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. distillationthe residue was purified by reverse phase silica gel column chromatography (elution solvent: distilled water, acetonitrile)

Sources & evidence

ORD record
ord-f49369bbff4040e4a3274ebf07f8df76
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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