Trifluoroacetic acid → cis(+/-)-3-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoic acid

HRID 1424969Notes

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][CH2:31][CH3:32])=[O:9])=[N:5][C:4]=1[C:33]([F:36])([F:35])[F:34])[CH3:2].FC(F)(F)C(O)=O>>[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][CH2:31][CH3:32])=[O:9])=[N:5][C:4]=1[C:33]([F:35])([F:36])[F:34])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86648507tert-Butyl cis(+/-)-3-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoate

Product 1

HCID 86648509cis(+/-)-3-(4-{[(5-Ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoic acidYield 86%

Procedure

The same operation as in Example (42f) was performed using tert-butyl cis(±)-3-(4-{[(5-ethyl-4-trifluoromethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)benzoate obtained in Example (48f) (80 mg, 0.16 mmol) and trifluoroacetic acid (1 ml), to obtain 61.1 mg of the title compound (86%).

Sources & evidence

ORD record: ord-f51ef9bf9d5b4f00a5899a2776378931
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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