Methanol → Hydroxycamptothecin

HRID 129524

반응식

HRID 129524 반응식
[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[NH:18][C:19]2[C:25](=[CH:26][C:14]=1[CH2:13]3)[CH:24]=[CH:23][C:21](=O)[CH:20]=2)=[O:11].C[OH:29].C(Cl)(Cl)Cl>FC(F)(F)C(O)=O>[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:25]([CH:24]=[C:23]([OH:29])[CH:21]=[CH:20]2)=[CH:26][C:14]=1[CH2:13]3)=[O:11]

참가 물질

5

반응물 3

HCID 887MethanolHCID 6212ChloroformHCID 178438218HCID 178438218, 화합물

생성물 1

HCID 97226Hydroxycamptothecin

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Naturally available mixture of 10 and 11-hydroxy camptothecin (1.0 g) is dissolved in anhydrous trifluoroacetic acid (5 ml) and anhydrous methanol (10 ml) to form a homogeneous solution of the quaternized components of the mixture. The homogeneous solution is then absorbed over enough silica gel (60 A; 60-230 mesh) to form a thick slurry. This slurry is dried by evaporating methanol and excess acid in vacuo on a rotary evaporator, leaving a powdery mass. The powder is then loaded over a pre-equilibrated silica gel column using chloroform. The column is washed using 1000 ml of a solvent mixture of 80% chloroform-20% methanol to remove non polar impurities, occluded trifluoroacetic acid and 11-hydroxcamptothecin (fraction A). Elution is then continued with chloroform-methanol-triethyl amine (in the approximate ratio of 1:1:0.01) and the band migrating away from the origin is collected using this eluent (Fraction B). Fractions A and B are evaporated separately and analyzed. Fraction B corresponds to the 10-hydroxy camptothecin isolate.

후처리

  1. customThe homogeneous solution is then absorbed over enough silica gel (60 A
  2. custom60-230 mesh) to form a thick slurry
  3. customThis slurry is dried
  4. customby evaporating methanol and excess acid in vacuo
  5. customon a rotary evaporator
  6. customleaving a powdery mass
  7. washThe column is washed
  8. addition1000 ml of a solvent mixture of 80% chloroform-20% methanol
  9. customto remove non polar impurities
  10. washElution
  11. customis collected
  12. customFractions A and B are evaporated separately

출처 및 근거

ORD 기록
ord-61912a077d134a629745505ed467e6c6
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468754

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