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

HRID 1090564Notes

Reaction equation

HRID 1090564 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([NH:14][C@H:15]([C:37]([N:39]3[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:41][CH2:40]3)=[O:38])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]S(C4C5C=CN=CC=5C=CC=4)(=O)=O)=[CH:19][CH:18]=3)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.[OH-].[K+].[Cl-].[Na+]>CO>[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11]([NH:14][C@H:15]([C:37]([N:39]3[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[CH2:41][CH2:40]3)=[O:38])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)(=[O:12])=[O:13])[C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 538846271-[N,O-Bis(5-Isoquinolinesulphonyl)Tyrosyl]-4-(3-Phenylpropyl)Piperazine

Product 1

HCID 536651241-[N-(5-Isoquinolinesulfonyl)Tyrosyl]-4-(3-Phenylpropyl)PiperazineYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. extractionextracted twice with 20 ml of a mixed solvent of chloroform/isopropanol (5:1)
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. washeluted with chloroform/methanol (40:1 to 10:1)

Sources & evidence

ORD record
ord-2cd53257955f40bfa14da0a9febb6751
Source dataset
uspto-grants-1992_01
Patent number
US05081246

Reaction notes

Loading…