Acetic Acid → Sodium Chloride
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].C(O)(=O)C.[Cl-:44].[Na+:45].O>>[Na+:45].[Cl-:44].[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
5
Conditions
- Temperature
- 0 °C
Procedure
When the doxorubicin peak is less than 0.1%, the reaction mixture is filtered through a coarse sintered glass funnel to remove the beads. A brine solution (at least 30% w/v) of 1.1 kg NaCl in 3.5 L water is prepared and cooled to 0° C. The filtered reaction mixture is then slowly added to the cooled brine solution with vigorous stirring over 45 minutes. The color of the solution must remain red, a blue solution indicates that the pH needs adjustment immediately to between 5.8–6.0 by adding acetic acid. The red precipitate is filtered through a medium sintered glass funnel, washed with water and dried under vacuum pressure over P2O5 to yield MeOSuc-Leu-Ala-Leu-Dox free of any residual doxorubicin.
Workup
- filtrationthe reaction mixture is filtered through a coarse sintered glass funnel
- customto remove the beads
- customThe filtered reaction mixture
- filtrationThe red precipitate is filtered through a medium sintered glass funnel
- washwashed with water
- dry with materialdried under vacuum pressure over P2O5
Sources & evidence
- ORD record
- ord-43810e51ab6145628b3b2eab9ae8e0d2
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214663B2
Reaction notes
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