HCID 22922163, compound → HCID 22922178, compound

HRID 2258527Notes

Reaction equation

HRID 2258527 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]([S:30][CH2:31][CH2:32][C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[S:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1>CO.[OH-].[Li+].O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]([S:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[S:30][CH2:31][CH2:32][C:33](=[O:37])[N:34]([CH3:36])[CH3:35])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 22922163HCID 22922163, compound

Product 1

HCID 22922178HCID 22922178, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3939Lithium HydroxideSolvent

Procedure

To a solution of 7-chloro-2-[5-{[2-(dimethylcarbamoyl)ethylthio](3-methoxycarbonylpropylthio)methyl}-benzofuran-2-yl]quinoline (0.49 g) in methanol (5 ml), 1N aqueous lithium hydroxide (1.32 ml) was added at ambient temperature under nitrogen atmosphere. After being stirred for 15 hours at ambient temperature, the resulting mixture was concentrated under reduced pressure to give a syrup. The syrup was dissolved in water, washed with diethyl ether, adjusted to pH 4 with diluted aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol. The fractions containing object compound were combined and concentrated in reduced pressure to give a syrup of 7-chloro-2-[5-{(3-carboxypropylthio)[2-(dimethylcarbamoyl)ethylthio]methyl}benzofuran-2-yl]quinoline (0.35 g).

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a syrup
  9. washeluted with a mixture of chloroform and methanol
  10. additionThe fractions containing object compound
  11. concentrationconcentrated in reduced pressure

Sources & evidence

ORD record
ord-8417d0f3e7ba430f919e86955cfeff0a
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

Loading…