Nitric Acid → Rubitecan

HRID 564696

Reaction equation

HRID 564696 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[N+:27]([O-])([OH:29])=[O:28]>S(=O)(=O)(O)O>[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16](=[CH:15][C:14]=1[CH2:13]3)[C:17]([N+:27]([O-:29])=[O:28])=[CH:18][CH:19]=[CH:20]2)=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 24360Camptothecin

Product 1

HCID 472335Rubitecan

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Camptothecin (25 g) in concentrated sulfuric acid (500 mL) was cooled in an ice-bath. To it was then added 70% nitric acid (30 mL), drop-wise to control the reaction temperature. The reaction mixture was then stirred for 36 hours, poured into excess crushed ice and the organic portion was extracted out using chloroform. The combined organic fraction was washed with freshly prepared 10% sodium bicarbonate solution and brine, and then dried over anhydrous sodium sulfate. Solvent was removed and the residue was purified by flash silica gel column using hexane/ethyl acetate (1:1) as eluent to furnish 2.7 g of 9-nitrocamptothecin.

Workup

  1. additionpoured
  2. custominto excess crushed ice
  3. extractionthe organic portion was extracted out
  4. washThe combined organic fraction was washed with freshly prepared 10% sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customSolvent was removed
  7. customthe residue was purified by flash silica gel column

Sources & evidence

ORD record
ord-cfa7149741544fb4a517ea3a14b046a3
Source dataset
uspto-grants-2001_01
Patent number
US06169080A

Linked notes

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