Reaction #5819

Reaction equation

amorphous compound

1-[N,O-Bis(5-Isoquinolinesulphonyl)Tyrosyl]-4-(3-Phenylpropyl)Piperazine

potassium hydroxide

sodium chloride

→

title compound

Yield 46.0%

1-[N-(5-Isoquinolinesulfonyl)Tyrosyl]-4-(3-Phenylpropyl)Piperazine

Yield 46.0%

Solvents

methanol

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed for 10 hours
2. 2
   Extractionextracted twice with 20 ml of a mixed solvent of chloroform/isopropanol (5:1)
3. 3
   DryingThe extract was dried over magnesium sulfate
4. 4
   Concentrationconcentrated under a reduced pressure
5. 5
   Washeluted with chloroform/methanol (40:1 to 10:1)

Procedure

216 mg of the amorphous compound obtained in Example 32 was dissolved in 3 ml of methanol, and to the solution was added 0.6 ml of 2N potassium hydroxide aqueous solution. The mixture was refluxed for 10 hours, and after the addition of 30 ml of saturated sodium chloride aqueous solution, extracted twice with 20 ml of a mixed solvent of chloroform/isopropanol (5:1). The extract was dried over magnesium sulfate and concentrated under a reduced pressure, and a resulting residue was applied to a silica gel column and eluted with chloroform/methanol (40:1 to 10:1) to obtain 74 mg of the title compound in a colorless amorphous form.

Source