N-(4-methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide → N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide

HRID 641136Notes

Reaction equation

HRID 641136 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])(=[O:27])=[O:26])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:5][CH:4]=1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:26])=[O:27])[C:10]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[C:14]3[O:22][CH:23]=[CH:24][C:13]=23)=[O:11])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 68637828N-(4-methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide

Product 1

HCID 68637975N-(4-Methoxy-phenyl)-N-(carboxypropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamideYield 87.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg (0.34 mmol) N-(4-Methoxy-phenyl)-N-(tert-butyl-oxycarbonylpropyl-sulfonyl)-furo[2,3-b]quinoline-4-carboxamide 9 were dissolved in 3.0 mL trifluoroacetic acid and stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure to give an yellow oil. The residue was purified by silica gel chromatography (eluent: methylene chloride/diethylether 6:4+0.1% acetic acid). Evaporation of the appropriate fractions gave 140 mg of the desired product 10.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give an yellow oil
  3. customThe residue was purified by silica gel chromatography (eluent: methylene chloride/diethylether 6:4+0.1% acetic acid)
  4. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-9f5ec1e2063e4877a1c70612ee2e9431
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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