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Formic Acid → 9-Aminocamptothecin

HRID 357501
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HRID 357501 반응식
[CH3:1][CH2:2][C@@:3]1([OH:29])[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:24](=[CH:25][C:14]=1[CH2:13]3)[C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=[CH:20]2)=[O:11].C(O)=O.C(N(CC)CC)C.C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][CH2:2][C@@:3]1([OH:29])[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:24]([C:23]([NH2:26])=[CH:22][CH:21]=[CH:20]2)=[CH:25][C:14]=1[CH2:13]3)=[O:11]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 297MethaneHCID 8471TriethylamineHCID 472335Rubitecan

생성물 1

HCID 724029-Aminocamptothecin수율 79.6%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 6228
Dimethylformamide
용매
2회

반응 조건

온도
80 °C

실험 절차

9-nitro camptothecin (3.4 g) was dissolved in distilled DMF (100 ml). Palladium acetate (0.08 g), formic acid (0.95 ml), and triethylamine (3.5 ml) were added. The solution was heated to 80° C., and the heating was continued for 1 hour. DMF (200 ml) and charcoal were added to the reaction mixture, and the stirring was continued for 0.5 hours at 80° C. The mixture was filtered hot through a celite filter aid, and the filtrate was concentrated to small volume. The precipitated orange solid was collected by filtration to yield 2.5 g of 9-amino camptothecin.

후처리

  1. waitthe stirring was continued for 0.5 hours at 80° C
  2. filtrationThe mixture was filtered hot through a celite
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated to small volume
  5. filtrationThe precipitated orange solid was collected by filtration

출처 및 근거

ORD 기록
ord-09dddc8345924d6c9f07196455a0bc84
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05840899

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