Dicyclohexylcarbodiimide → Camptothecin

HRID 1674452Notes

Reaction equation

HRID 1674452 reaction equation
NCC(O)=O.[CH3:6][CH2:7][C@@:8]1([OH:31])[C:13](=[O:14])[O:12][CH2:11][C:10]2[C:15]([N:17]3[C:29](=[CH:30][C:9]1=2)[C:28]1[N:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[CH:20][C:19]=1[CH2:18]3)=[O:16].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:6][CH2:7][C@@:8]1([OH:31])[C:13](=[O:14])[O:12][CH2:11][C:10]2[C:15]([N:17]3[C:29](=[CH:30][C:9]1=2)[C:28]1[N:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[CH:20][C:19]=1[CH2:18]3)=[O:16]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 86600219HCID 86600219, compound

Product 1

HCID 24360Camptothecin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The synthesis is shown in FIG. 6. 1 g of Y-shape branched PEG carboxylic acid (Example 5 or 6) was dissolved in 10 ml dichloromethane. 120 mg of glycine-camptothecin, 50 mg of dimethylamino pyridine and 95 mg of dicyclohexylcarbodiimide were added to the solution. The solution was stirred at room temperature for 6 hours. The solvent was removed under vacuum. The residue was dissolved in 20 ml of 1,4-dioxane. The precipitate was removed by filtration. The solution was concentrated, and the residue was added to 20 ml of ethyl ether. The precipitate was collected by filtration, washed with ethyl ether and dried under vacuum. Yield: 0.8 g (80%), Mp: 56-58° C.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in 20 ml of 1,4-dioxane
  3. customThe precipitate was removed by filtration
  4. concentrationThe solution was concentrated
  5. additionthe residue was added to 20 ml of ethyl ether
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with ethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-379762b971714296bd40cecbf12c38fe
Source dataset
uspto-grants-2011_08
Patent number
US08003089B2

Reaction notes

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