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

HRID 1587185Notes

Reaction equation

HRID 1587185 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 2 N 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-1ab787a3ac334b11b5d5e54c1195bfc7
Source dataset
uspto-grants-1993_06
Patent number
US05216150

Reaction notes

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