1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131723122, compound

HRID 1700248Notes

Reaction equation

HRID 1700248 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].[CH2:27]1[O:40][C:39]2[CH:38]=[CH:37][C:31]([O:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:30][C:29]=2[O:28]1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[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].[CH2:27]1[O:40][C:39]2[CH:38]=[CH:37][C:31]([O:32][CH2:33][C:34]([O-:36])=[O:35])=[CH:30][C:29]=2[O:28]1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24360CamptothecinHCID 1531512(1,3-benzodioxol-5-yloxy)acetic acid

Product 1

HCID 131723122HCID 131723122, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The mixture of camptothecin (10 mg, 0.029 mmol), 3,4-methylenedioxyphenoxyacetic acid (8 mg, 0.042 mmol), EDCI (28 mg, 0.15 mmol), DMAP (2 mg, 0.02 mmol) and dichloromethane (3 ml) was stirred in the room temperature for 20 h, then dichloromethane (20 ml) was added to the solution. Organic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (10 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting solid was separated by column chromatography (eluent: CHCl3:CH3OH 9:1) to afford 8 mg camptothecin-20-O-3,4-methylenedioxyphenoxyacetate, yield: 53.0%, mp.

Workup

  1. washOrganic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (10 ml) and brine (20 ml)
  2. dry with materialdried over MgSO4
  3. customAfter the solvent was removed under reduced pressure
  4. customthe resulting solid was separated by column chromatography (eluent: CHCl3:CH3OH 9:1)

Sources & evidence

ORD record
ord-b46751e3b43b4963823f6481a8aaad15
Source dataset
uspto-grants-2002_02
Patent number
US06350756B1

Reaction notes

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