Pristinamycin → Virginiamycin M1

HRID 1081924

Reaktionsgleichung

Reaktionsgleichung von HRID 1081924
CCC1NC(=O)C(NC(C2N=CC=CC=2O)=O)C(C)OC(=O)C(C2C=CC=CC=2)NC(=O)C2N(CCC(C2)=O)C(=O)C(CC2C=CC=CC=2)N(C)C(=O)C2N(CCC2)C1=O.[CH3:61][CH:62]1[CH:93]([CH:94]([CH3:96])[CH3:95])[O:92][C:90](=[O:91])[C:89]2[N:85]([CH2:86][CH2:87][CH:88]=2)[C:83](=[O:84])[C:80]2=[CH:81][O:82][C:78](=[N:79]2)[CH2:77][C:75](=[O:76])[CH2:74][CH:73]([OH:97])[CH:72]=[C:71]([CH3:98])[CH:70]=[CH:69][CH2:68][NH:67][C:65](=[O:66])[CH:64]=[CH:63]1>C(Cl)Cl>[CH3:61][C@H:62]1[C@@H:93]([CH:94]([CH3:95])[CH3:96])[O:92][C:90](=[O:91])[C:89]2[N:85]([CH2:86][CH2:87][CH:88]=2)[C:83](=[O:84])[C:80]2=[CH:81][O:82][C:78](=[N:79]2)[CH2:77][C:75](=[O:76])[CH2:74][C@H:73]([OH:97])[CH:72]=[C:71]([CH3:98])[CH:70]=[CH:69][CH2:68][NH:67][C:65](=[O:66])[CH:64]=[CH:63]1

Komponenten

3

Edukt 1

HCID 11979535Pristinamycin

Produkt 1

HCID 5459319Virginiamycin M1Ausbeute 0,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A simplified modification of the procedure of Sharma, et el. is suitable for use in the invention. In this procedure, 500 g STAFAC® is placed in an Erlenmeyer flask with 3.75 L methylene chloride. The mixture is stirred overnight with a mechanical stirrer. The STAFAC® is filtered, and rinsed with a Buchner funnel under vacuum, giving a cloudy yellow solution. A second filtration is performed through a glass-frit (medium) filter, giving a clear yellow solution. This solution is concentrated in vacuo to give a crude mixture of VM and VS. 10 g of this yellow/brown solid is purified with a medium pressure liquid chromatography (MPLC) column using gradients of 0.5, 1, 1.5, 3, 4, 6 and 8% methyl alcohol in methylene chloride. The fractions are separated by thin layer chromatography, and the fraction containing VM is concentrated with rotary evaporation. The VM1 is then recrystallized using ethyl acetate. 1.105 g of virginiamycin M1 is obtained.

Aufarbeitung

  1. filtrationThe STAFAC® is filtered
  2. washrinsed with a Buchner funnel under vacuum
  3. customgiving a cloudy yellow solution
  4. filtrationA second filtration
  5. filtrationfilter
  6. customgiving a clear yellow solution
  7. concentrationThis solution is concentrated in vacuo
  8. customto give a crude
  9. additionmixture of VM and VS
  10. custom10 g of this yellow/brown solid is purified with a medium pressure liquid chromatography (MPLC) column
  11. customThe fractions are separated by thin layer chromatography
  12. additionthe fraction containing VM
  13. concentrationis concentrated with rotary evaporation
  14. customThe VM1 is then recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-2953ea09ad214178a1f415aabe2c45e3
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587475

Verknüpfte Notizen

Wird geladen…