Reaction #1055631

Reaction equation

CH3OH CH2Cl2

doxorubicin hydrochloride

diisopropylethylamine

diisopropylethylamine

→

Doxorubicin

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGstirred for an additional 31 h
2. 2
   OtherThe solvent was removed under reduced pressure
3. 3
   Otherthe residue was chromatographed on a short silica column
4. 4
   Washeluting with 5% methanol in dichloromethane
5. 5
   OtherThe product obtained
6. 6
   Otherprecipitated with ether
7. 7
   FiltrationThe red solid was filtered
8. 8
   Washrinsed with ether
9. 9
   Otherdried under vacuum at room temperature

Procedure

A mixture of doxorubicin hydrochloride (58.5 mg, 0.10 mmol), phosphorylating agent (26.7 mg, 0.12 mmol) and diisopropylethylamine (45.5 μL, 0.26 mmol) in 3.0 mL of DMF was stirred for 19 h at room temperature. Treated with additional diisopropylethylamine (60 μL, 0.34 mmol) and phosphorylating agent (31.8 mg, 0.14 mmol) and stirred for an additional 31 h. The solvent was removed under reduced pressure and the residue was chromatographed on a short silica column eluting with 5% methanol in dichloromethane. The product obtained was treated with CH3OH/CH2Cl2 and precipitated with ether. The red solid was filtered, rinsed with ether and dried under vacuum at room temperature.

Source