Citric Acid → 1-Benzyloxycarbonyl-4-[N-(5-isoquinolinesulfonyl)tyrosyl]homopiperazine

HRID 1587194

Reaktionsgleichung

Reaktionsgleichung von HRID 1587194
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:55])[C@H:19]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41]S(C3C4C=CN=CC=4C=CC=3)(=O)=O)=[CH:37][CH:36]=2)[NH:20][S:21]([C:24]2[C:25]3[CH:26]=[CH:27][N:28]=[CH:29][C:30]=3[CH:31]=[CH:32][CH:33]=2)(=[O:23])=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:55])[C@H:19]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[NH:20][S:21]([C:24]2[C:25]3[CH:26]=[CH:27][N:28]=[CH:29][C:30]=3[CH:31]=[CH:32][CH:33]=2)(=[O:22])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 538376321-Benzyloxycarbonyl-4-[N,O-Bis(5-Isoquinolinesulfonyl)Tyrosyl]Homopiperazine

Produkt 1

HCID 228421921-Benzyloxycarbonyl-4-[N-(5-isoquinolinesulfonyl)tyrosyl]homopiperazineAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5.50 g of the amorphous compound obtained in Example 122 was dissolved in 30 ml of methanol and 30 ml of tetrahydrofuran, to the solution was added 60 ml of 1N sodium hydroxide, and the mixture was refluxed for 2 hours and then cooled. The reaction mixture was acidified with citric acid and then alkalized with sodium bicarbonate, resulting insoluble matter was dissolved with a small amount of methanol, and the solution was extracted twice with 400 ml of chloroform. The extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with chloroform/methanol (20:1) to obtain 3.1 g of the title compound in a colorless amorphous form.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customresulting insoluble matter
  4. extractionthe solution was extracted twice with 400 ml of chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under a reduced pressure
  8. customresulting residue
  9. washeluted with chloroform/methanol (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-6f5b34a83fba490abab0d654c9a8dac2
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216150

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