Pristinamycin → Virginiamycin M1

HRID 1081924

반응식

HRID 1081924 반응식
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

참가 물질

3

반응물 1

HCID 11979535Pristinamycin

생성물 1

HCID 5459319Virginiamycin M1수율 0.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2953ea09ad214178a1f415aabe2c45e3
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587475

연결된 노트

불러오는 중…