Trifluoroacetic acid → HCID 22184998, compound

HRID 890397Notes

Reaction equation

HRID 890397 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:28][C:29]([C:31]2[CH:40]=[C:39]([O:41][CH2:42][C:43]([O:45]C(C)(C)C)=[O:44])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)=[O:30])[CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[O:18])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12]([CH:14]([NH:28][C:29]([C:31]2[CH:40]=[C:39]([O:41][CH2:42][C:43]([OH:45])=[O:44])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)=[O:30])[CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22185029HCID 22185029, compound

Product 1

HCID 22184998HCID 22184998, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-3-(((1,1-dimethylethoxy)carbonyl)methoxy)carbonylpropyl]aminocarbonyl-4-((1,1-dimethylethoxy)carbonyl)methoxyquinoline (38 mg, 0.05 mmol) in 1 mL CH2Cl2, was added 2 mL trifluoroacetic acid, then the reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was evaporated in vacuo to afford an oil. The oil was diluted in water (5 mL), adjusted to pH 4.5 by saturated NaHCO3, then extracted by ethyl acetate (3×10 mL). The organic layer was evaporated in vacuo to afford 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-3-((carboxy)methoxycarbonyl)propyl]aminocarbonyl-4-(carboxy)methoxyquinoline as a white solid (30 mg); NMR (DMSO-d6), 1.16 (t, 3), 1.90 (m, 1), 2.10 (m, 1), 2.45 (m, 2), 3.3–3.9 (m, 8), 4.02 (q, 2), 4.52 (q, 2), 5.04 (m, 1), 5.13 (s, 2), 7.46 (s, 1), 7.68 (t, 1), 7.84 (t, 1), 8.08 (d, 1), 8.23 (d, 1), 9.95 (m, 1) ppm.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford an oil
  3. extractionextracted by ethyl acetate (3×10 mL)
  4. customThe organic layer was evaporated in vacuo

Sources & evidence

ORD record
ord-f623ea8dfc544158977f4a00158dc739
Source dataset
uspto-grants-2006_02
Patent number
US06995156B2

Reaction notes

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