Isopropanol → Isopropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19](OC)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH:34]([OH:37])([CH3:36])[CH3:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:37][CH:34]([CH3:36])[CH3:35])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of 0.312 g methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate in 5 mL isopropanol is added a solution of a catalytic amount of sodium hydride in 1 mL isopropanol. The mixture is refluxed for 18 hours and the solvent is evaporated. The residue is dissolved in methylene chloride and the solution is washed with saturated ammonium chloride solution. The organic phase is dried, filtered, evaporated to give a clear oil which is purified by flash column chromatography using ethyl acetate and hexane (2:3) as the eluent to give as a clear oil isopropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate.
Workup
- temperatureThe mixture is refluxed for 18 hours
- customthe solvent is evaporated
- dissolutionThe residue is dissolved in methylene chloride
- washthe solution is washed with saturated ammonium chloride solution
- customThe organic phase is dried
- filtrationfiltered
- customevaporated
- customto give a clear oil which
- customis purified by flash column chromatography
Sources & evidence
- ORD record
- ord-4ba60d17d662474b9e6a7b8591fdcdea
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05025025
Reaction notes
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