Formic Acid → 9-Aminocamptothecin

HRID 357501

Reaction equation

HRID 357501 reaction equation
[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]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 297MethaneHCID 8471TriethylamineHCID 472335Rubitecan

Product 1

HCID 724029-AminocamptothecinYield 79.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-09dddc8345924d6c9f07196455a0bc84
Source dataset
uspto-grants-1998_11
Patent number
US05840899

Linked notes

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