Potassium Carbonate → N-(4-(4-(Ethyl(6-hydroxy-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

HRID 1654299Notes

Reaction equation

HRID 1654299 reaction equation
[CH2:1]([N:3]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:28]C(=O)C)([CH3:27])[CH3:26])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O>[CH2:1]([N:3]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:28])([CH3:27])[CH3:26])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:11][CH:10]=1)[OH:8])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 15294456N-(4-(4-(Ethyl(6-acetoxy-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 15294457N-(4-(4-(Ethyl(6-hydroxy-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamideYield 89.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of the product from Example 13 (1.35 g, 0.00296 mol) in methanol (80 ml) was treated with a solution of K2CO3 (2.04 g, 0.0148 mol) in water (5.9 ml) and the mixture was refluxed for 21.5 hours. It was kept at ambient temperature for 42.5 hours and concentrated to an aqueous residue which was mixed with water (10 ml) and CH2Cl2, acidified to pH 8.5-9 with 6 NHCl, saturated with NaCl and extracted with CH2Cl2. The extract was dried (MgSO4), concentrated and the residue chromatographed on silica gel with 0.5% NH4OH-9% MeOH--CH2Cl2 to give 1.1 g of the titled compound which is a compound of Formula I'. The high resolution mass spectrum had m/z 414(M+). Theory for C21H38N2O4S: 414.2552; measured: 414.2560.

Workup

  1. temperaturethe mixture was refluxed for 21.5 hours
  2. concentrationconcentrated to an aqueous residue which
  3. additionwas mixed with water (10 ml) and CH2Cl2
  4. extractionextracted with CH2Cl2
  5. dry with materialThe extract was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue chromatographed on silica gel with 0.5% NH4OH-9% MeOH

Sources & evidence

ORD record
ord-4103e2810d4c4e10bf150b4c59b1a6e2
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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