Isopropanol → Isopropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate

HRID 465547Notes

Reaction equation

HRID 465547 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]=1

Participants

4

Reactant 3

HCID 3776Isopropanol2×HCID 24758Sodium hydrideHCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Product 1

HCID 14986667Isopropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate

Procedure

To a solution of 0.312 g methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate (example 4a) 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 h 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/hexane (2:3) as the eluent to give as a clear oil isopropyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate.

Workup

  1. temperatureThe mixture is refluxed for 18 h
  2. customthe solvent is evaporated
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washthe solution is washed with saturated ammonium chloride solution
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a clear oil which
  9. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-4fb9a2a1eaec4c2cb0ac048e223168b1
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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