Dimethylamine → Camptothecin

HRID 275055

Reaction equation

HRID 275055 reaction equation
[CH3:1][CH2:2][CH:3]1[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[C:14](=[CH:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11].CNC.CN(C=[O:33])C>O=O.[Cu](Cl)Cl>[CH3:1][CH2:2][C@@:3]1([OH:33])[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]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 266552Npc28848

Product 1

HCID 24360CamptothecinYield 91%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 977OxygenSolvent

Procedure

To a solution of 18 (47.8 mg, 0.144 mmol), copper(II) chloride (80 mg) and dimethylamine (100 μl ) in DMF (16 mL) was bubbled in oxygen for 7 h. The reaction mixture was concentrated in vacuum to about 5 mL, and was then diluted with water. .A solution of saturated ammonium chloride was used to adjusted the pH of the above mixture to about 6, and the resulting mixture was extracted with chloroform (10 mL×10). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 2% methanol in chloroform to give dl-camptothecin (45.5 mg, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum to about 5 mL
  2. additionwas then diluted with water
  3. extractionthe resulting mixture was extracted with chloroform (10 mL×10)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed with 2% methanol in chloroform

Sources & evidence

ORD record
ord-42e02c0e42f942e7baf497f5fc548621
Source dataset
uspto-grants-1995_02
Patent number
US05391745

Linked notes

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