Trifluoroacetic acid methylene chloride → Trifluoroacetic acid
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:24][C:25]([C:27]2[CH:36]=[C:35]([O:37][C:38]3([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:41][CH2:40][CH2:39]3)[C:34]3[C:29](=[CH:30][C:31]([CH3:47])=[CH:32][CH:33]=3)[N:28]=2)=[O:26])[CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].C(Cl)Cl>>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:24][C:25]([C:27]2[CH:36]=[C:35]([O:37][C:38]3([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:39][CH2:40][CH2:41]3)[C:34]3[C:29](=[CH:30][C:31]([CH3:47])=[CH:32][CH:33]=3)[N:28]=2)=[O:26])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]Participants
Reactant 2
Product 2
Procedure
A solution of 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-3-(1,1-dimethylethoxycarbonyl)propyl]aminocarbonyl-7-methyl-4-(1-(ethoxycarbonyl)cyclobut-1-oxy)quinoline (75 mg, 0.09 mmol) in 50% trifluoroacetic acid-methylene chloride (2 ml) was stirred at ambient temperature for 1 hour. The solvent was evaporated in vacuo and the resulting residue was purified by preparative HPLC to afford 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-3-carboxypropyl]aminocarbonyl-7-methyl-4-(1-(ethoxycarbonyl)cyclobut-1-oxy)quinoline as a white solid (60 mg, 93%, trifluoroacetic acid salt); NMR (DMSO-d6) 1.03 (t, 3), 1.16 (t, 3), 1.82 (m, 1), 2.00 (m, 3), 2.26 (m, 2), 2.55 (s, 3), 2.59 (m, 2), 2.77 (m, 2), 3.38 (m, 6), 3.60 (m, 2), 4.02 (q, 2), 4.12 (q, 2), 4.98 (m, 1), 6.92 (s, 1), 7.52 (d, 1), 7.88 (s, 1), 8.14 (d, 1), 8.85 (d, 1) ppm.
Workup
- customThe solvent was evaporated in vacuo
- customthe resulting residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-11338e78d40a41e79fabb792889ca5a0
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026323B2
Reaction notes
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