Reaktion #2061503

Reaktionsgleichung

hydrazine hydrate

water

N-(5-acetoxypentanoyloxy)succinimide

C1

gentamicins

→

ammonium hydroxide

Ausbeute 7.0%

1-N-(5-hydroxypentanoyl)-5-epigentamicin

gentamicins

Lösungsmittel

chloroform

triethylamine

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONDissolve 2.5 g
2. 2
   workup.ADDITIONAdd 0.35 g
3. 3
   workup.ADDITIONAdd a solution of 1.0 g
4. 4
   SonstigeEvaporate the solution in vacuo
5. 5
   Sonstigeto leave a solid residue
6. 6
   workup.DISSOLUTIONDissolve the residue in 5 ml
7. 7
   Temperaturunder reflux for 15 minutes
8. 8
   EinengenConcentrate the solution in vacuo
9. 9
   Sonstigeto leave an oily residue and chromatograph it on 200 g

Vorschrift

Dissolve 2.5 g. of 5-epigentamicin C1 in 250 ml. of water and add 100 ml. of methanol. Add 0.35 g. of triethylamine and stir for fifteen minutes. Add a solution of 1.0 g. of N-(5-acetoxypentanoyloxy)succinimide with stirring to the solution of the antibiotic, and stir at ambient temperature for 16 hours. Evaporate the solution in vacuo to leave a solid residue. Dissolve the residue in 5 ml. of 5% ethanolic hydrazine hydrate and heat under reflux for 15 minutes. Concentrate the solution in vacuo to leave an oily residue and chromatograph it on 200 g. silica gel in the lower phase of a solvent system consisting of chloroform:methanol:7% ammonium hydroxide (2:1:1) to give 1-N-(5-hydroxypentanoyl)-5-epigentamicin C1.

Quelle