Sodium Hydroxide → N-[2-(4-Benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl}-N-(2-hydroxyethyl)-5-isoquinolinesulfonamide

HRID 1587197Notes

Reaction equation

HRID 1587197 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([CH:21]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:25][CH2:24]1)[S:8]([C:11]1[C:12]2[CH:13]=[CH:14][N:15]=[CH:16][C:17]=2[CH:18]=[CH:19][CH:20]=1)(=[O:10])=[O:9])(=O)C.[OH-].[Na+]>CO.O1CCCC1.O>[CH2:32]([O:31][C:29]([N:26]1[CH2:25][CH2:24][N:23]([CH2:22][CH:21]([N:7]([CH2:6][CH2:5][OH:4])[S:8]([C:11]2[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=[CH:19][CH:20]=2)(=[O:9])=[O:10])[CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[CH2:28][CH2:27]1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 19796392N-(2-Acetoxyethyl)-N-[2-(4-benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl]-5-isoquinolinesulfonamide

Product 1

HCID 19796287N-[2-(4-Benzyloxycarbonylpiperazinyl)-1-(p-methoxybenzyl)ethyl}-N-(2-hydroxyethyl)-5-isoquinolinesulfonamideYield 71.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

600 mg of the amorphous compound obtained in Example 138 was dissolved in 6 ml of methanol and 3 ml of tetrahydrofuran, to the solution was added 6 ml of 1N sodium hydroxide aqueous solution, and the mixture was stirred at a room temperature for 2 hours. The reaction mixture was diluted with water and extracted twice with 50 ml of chloroform, and the extract was washed with saturated sodium chloride aqueous solution, dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure. Resulting oil was applied to a silica gel column and eluted with chloroform/methanol (100:1 to 50:1) to obtain 403 mg of the title compound in a colorless amorphous form.

Workup

  1. extractionextracted twice with 50 ml of chloroform
  2. washthe extract was washed with saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under a reduced pressure
  6. customResulting oil
  7. washeluted with chloroform/methanol (100:1 to 50:1)

Sources & evidence

ORD record
ord-3a110464a0b64795a18dcf53f8322624
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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