Potassium Hydroxide → HCID 22132607, compound

HRID 1856769Notes

Reaction equation

HRID 1856769 reaction equation
[CH3:1][N:2]([CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH:28]=[CH:27]2)[C:3]([N:5]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:6][CH:7]([O:10]C(=O)C)[CH2:8][CH3:9])=[O:4].[OH-].[K+]>CO>[CH3:1][N:2]([CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH:28]=[CH:27]2)[C:3]([N:5]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH2:6][CH:7]([OH:10])[CH2:8][CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22132588HCID 22132588, compound

Product 1

HCID 22132607HCID 22132607, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-{3-[1-Methyl-3-cyclohexyl-3-(2-acetyloxybutyl)ureido]propoxy}-carbostyril (1.63 g) is added to methanol (10 ml), and thereto is added dropwise a 10% aqueous potassium hydroxide solution (10 ml). The mixture is stirred at room temperature overnight, and concentrated under reduced pressure to remove the solvent. The resultant is poured into water, and extracted with chloroform. The extract is concentrated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20: 1), and recrystallized from methylene chloride-diethyl ether to give 6-{3-[1-methyl-3-cyclohexyl-3-(2-hydroxybutyl)ureido]propoxy}carbostyril (0.6 g) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvent
  3. additionThe resultant is poured into water
  4. extractionextracted with chloroform
  5. concentrationThe extract is concentrated under reduced pressure
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography (solvent; methylene chloride:methanol=20: 1)
  8. customrecrystallized from methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-f395ffc16827417db240f67575a880cd
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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