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

HRID 5721Notes

Reaction equation

HRID 5721 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][NH:42][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.[CH2:45]([O:52][C:53](Cl)=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[Cl-].[Na+].[OH-].[Na+]>C(Cl)Cl.CO.C(N(CC)CC)C>[CH2:45]([O:52][C:53]([N:42]1[CH2:41][CH2:40][N:39]([C:37](=[O:38])[C@H:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[NH:14][S:11]([C:6]2[C:5]3[CH:4]=[CH:3][N:2]=[CH:1][C:10]=3[CH:9]=[CH:8][CH:7]=2)(=[O:12])=[O:13])[CH2:44][CH2:43]1)=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 542919501-[N,O-Bis(5-Isoquinolinesulfonyl)Tyrosyl]Piperazine

Product 1

HCID 542409841-Benzyloxycarbonyl-4-[N-(5-Isoquinolinesulfonyl)Tyrosyl]Piperazine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

620 mg of the crude product obtained in Example 28 was dissolved in 10 ml of methylene chloride, and to the solution were sequentially added 0.29 ml of benzyloxycarbonyl chloride and 3.04 ml of triethylamine with ice cooling. After stirring for two hours with ice cooling, 40 ml of saturated sodium chloride aqueous solution was added to the reaction mixture, which was then extracted twice with 20 ml of chloroform, and the extract was dried over magnesium sulfate and concentrated under a reduced pressure to obtain a residue. The residue was dissolved in 6 ml of methanol, and after the addition of 2 ml of 1N sodium hydroxide aqueous solution, the mixture was refluxed for two hours, dried over magnesium sulfate and concentrated under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with chloroform/methanol (80:1 to 50:1) to obtain 336 mg of the title compound as colorless crystals.

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionwas then extracted twice with 20 ml of chloroform
  3. dry with materialthe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customto obtain a residue
  6. temperaturethe mixture was refluxed for two hours
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. washeluted with chloroform/methanol (80:1 to 50:1)

Sources & evidence

ORD record
ord-16583531d898465db747873666a6aa4e
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Reaction notes

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