Water → Ammonium Hydroxide

HRID 1974320

Reaktionsgleichung

Reaktionsgleichung von HRID 1974320
[CH3:1][CH:2]([NH:32][CH3:33])[CH:3]1[O:8][CH:7]([O:9][CH:10]2[CH:15]([OH:16])[CH:14]([O:17][CH:18]3[O:23][CH2:22][C:21]([OH:25])([CH3:24])[CH:20]([NH:26][CH3:27])[CH:19]3[OH:28])[CH:13]([NH2:29])[CH2:12][CH:11]2[NH2:30])[CH:6]([NH2:31])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=O.O.C1(=O)N(CCCCC(ON2C(=O)CCC2=O)=O)C(=O)C2=CC=CC=C12>CO.C(Cl)(Cl)Cl.CN(C)C=O.C(N(CC)CC)C>[OH-:8].[NH4+:26].[CH3:1][CH:2]([NH:32][CH3:33])[CH:3]1[O:8][CH:7]([O:9][CH:10]2[CH:15]([OH:16])[CH:14]([O:17][CH:18]3[O:23][CH2:22][C:21]([OH:25])([CH3:24])[CH:20]([NH:26][CH3:27])[CH:19]3[OH:28])[CH:13]([NH2:29])[CH2:12][CH:11]2[NH2:30])[CH:6]([NH2:31])[CH2:5][CH2:4]1

Komponenten

10

Edukt 4

HCID 962WaterHCID 1117Sulfate IonHCID 3467GentamicinHCID 21489017N-(5-phthalimidopentanoyloxy)succinimide

Produkt 2

HCID 3467GentamicinHCID 14923Ammonium HydroxideAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittel2×HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Dissolve 2.5 g. of 5-epigentamicin C1 sulfate in 250 ml. of water and add 100 ml. of methanol. Add 0.35 g. of triethylamine and stir for 10 minutes. Add a solution of 1.2 g. N-(5-phthalimidopentanoyloxy)succinimide in 20 ml. of dry dimethylformamide dropwise with stirring to the solution of the antibiotic. Stir the mixture at ambient temperature for 16 hours. Concentrate the reaction mixture to a residue in vacuo and triturate the residue with methanol to yield 3.4 g. of white solids. Chromatograph the residue on 200 g. of silica gel in the lower phase of a chloroform:methanol:7% ammonium hydroxide (2:1:1) system to give 1-N-(5-phthalimidopentanoyl)-5-epigentamicin C1.

Aufarbeitung

  1. dissolutionDissolve 2.5 g
  2. additionAdd 0.35 g
  3. additionAdd a solution of 1.2 g
  4. concentrationConcentrate the reaction mixture to a residue in vacuo
  5. customtriturate the residue with methanol
  6. customto yield 3.4 g

Quellen und Nachweise

ORD-Eintrag
ord-a0e3067d61fa4680abea436c25050f13
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US04000261

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