Doxorubicin Hydrochloride → Doxorubicin

HRID 929375Notes

Reaction equation

HRID 929375 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[CH2:12][C@@:11]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:38])[C@@H:3]1[OH:39].Cl>CN(C=O)C>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[CH2:12][C@@:11]([OH:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:38])[C@@H:3]1[OH:39]

Participants

3

Reactant 1

HCID 443939Doxorubicin Hydrochloride

Product 1

HCID 31703Doxorubicin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-e0d1f7fffcc24ea8945d863e3c6b199a
Source dataset
uspto-grants-2016_03
Patent number
US09295731B2

Reaction notes

Loading…