Water → ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]acrylate

HRID 1986437Notes

Reaction equation

HRID 1986437 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:10]2[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)(=O)=O.C(N(CC)CC)C.[C:46]([O:50][CH2:51][CH3:52])(=[O:49])[CH:47]=[CH2:48].O>CN(C)C=O>[C:26]([O:25][C:23]([NH:22][CH2:21][C:11]1[C:12]([CH2:17][CH:18]([CH3:20])[CH3:19])=[N:13][C:14]2[C:9]([C:10]=1[C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[CH:8][C:7](/[CH:48]=[CH:47]/[C:46]([O:50][CH2:51][CH3:52])=[O:49])=[CH:16][CH:15]=2)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 510503433-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl trifluoromethanesulfonate

Product 1

HCID 51050344ethyl (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]acrylateYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl trifluoromethanesulfonate (1.5 g, 2.8 mmol) in N,N-dimethylformamide (10 ml) were added dichlorobistriphenylphosphine palladium (0.021 g, 0.030 mmol), triethylamine (4.2 ml, 30 mmol) and ethyl acrylate (0.65 ml, 6.0 mmol) and the mixture was stirred at 70° C. 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 (2E)-3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]acrylate (0.87 g, yield 62%) 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-c8133c1a12bd4d8182cabd1af23998a6
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

Loading…