Water → Ethyl 4-({[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}methyl)-2-furoate

HRID 1986440Notes

Reaction equation

HRID 1986440 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:5]2[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.[C:32](=O)([O-])[O-].[K+].[K+].ClC[C:40]1[O:44][C:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:42][CH:41]=1.O>CN(C)C=O>[C:20]([O:19][C:18]([NH:17][CH2:16][C:6]1[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:8][C:9]2[C:4]([C:5]=1[C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1)=[CH:3][C:2]([O:1][CH2:32][C:41]1[CH:42]=[C:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[O:44][CH:40]=1)=[CH:11][CH:10]=2)=[O:24])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 51050241HCID 51050241, compound

Product 1

HCID 68828216Ethyl 4-({[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}methyl)-2-furoateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {[6-hydroxy-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.40 g, 0.95 mmol) in N,N-dimethylformamide (10 ml) were added potassium carbonate (0.28 g, 2.0 mmol) and ethyl 5-chloromethyl-2-furancarboxylate (0.38 g, 2.0 mmol) and the mixture was stirred at room temperature for 6 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl 4-({[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}methyl)-2-furoate (0.43 g, yield 80%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-43b6c71d5c3f40838e445173c47ef9a0
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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