Reaction #1016557

ord-e0d1f7fffcc24ea8945d863e3c6b199a

Reaction equation

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
doxorubicin HCl
→
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
compound ( 1 )
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Doxorubicin

Reactants

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
doxorubicin HCl
—
compound ( 1e )
—
TEA

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated under vacuum
  2. 2
    OtherThe crude was purified by reverse-phase C-18 High Performance Liquid Chromatography (HPLC)

Procedure

A mixture of compound (1e) (25.25 mg) and doxorubicin HCl (1.0 eq) and TEA (1.0 eq) in DMF (0.40 mL) was stirred at room temperature for 1 h and then concentrated under vacuum. The crude was purified by reverse-phase C-18 High Performance Liquid Chromatography (HPLC) using acetonitrile/aqueous buffer as eluent to provide compound (1).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09295731B2uspto-grants-2016_03