Trifluoroacetic acid → Trifluoroacetate

HRID 2105881Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[O:30])[CH2:24][CH2:23]3)=[O:21])[C:10]([C:37]3[C:38]([O:52][CH2:53][CH3:54])=[CH:39][C:40]([Cl:51])=[C:41]([S:43]([NH:46]C(C)(C)C)(=[O:45])=[O:44])[CH:42]=3)=[N:9]2)=[CH:4][CH:3]=1.[F:55][C:56]([F:61])([F:60])[C:57]([OH:59])=[O:58]>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[O:30])[CH2:24][CH2:23]3)=[O:21])[C:10]([C:37]3[C:38]([O:52][CH2:53][CH3:54])=[CH:39][C:40]([Cl:51])=[C:41]([S:43]([NH2:46])(=[O:45])=[O:44])[CH:42]=3)=[N:9]2)=[CH:4][CH:3]=1.[F:55][C:56]([F:61])([F:60])[C:57]([O-:59])=[O:58]

Participants

Conditions

Temperature: 80 °C

Procedure

5-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxy-benzenesulfonamide (˜10 mg) was dissolved in 2 mL of trifluoroacetic acid and heated to 80° C. for 30 min. The reaction mixture was diluted with 2 mL of methylene chloride and 1.5 mL of 10% potassium carbonate solution then agitated. The organic layer was separated and concentrated in vacuo to give 5-{(4S,5R)-4,5-bis-(4-chloro-phenyl)-1-[4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazine-1-carbonyl]-4,5-dihydro-1H-imidazol-2-yl}-2-chloro-4-ethoxy-benzenesulfonamide as trifluoroacetate salt. LC-MS: 763.3 [(M+H)+].

Workup

customThe organic layer was separated
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-edf272debd6c4d36a6b17ce336cba1e7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579368B2

Reaction notes

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