Doxorubicin Hydrochloride → HCID 131727237, compound

HRID 1684886Notes

Reaction equation

HRID 1684886 reaction equation
[C:1]([O-:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.[K+].[CH3:13][C@@H:14]1[O:19][C@@H:18]([O:20][C@@H:21]2[C:26]3=[C:27]([OH:44])[C:28]4[C:40](=[O:41])[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][C:38]=5[O:42][CH3:43])[C:32](=[O:33])[C:29]=4[C:30]([OH:31])=[C:25]3[CH2:24][C@@:23]([OH:49])([C:45]([CH2:47][OH:48])=[O:46])[CH2:22]2)[CH2:17][C@H:16]([NH2:50])[C@@H:15]1[OH:51].Cl>O>[CH3:13][C@@H:14]1[O:19][C@@H:18]([O:20][C@@H:21]2[C:26]3=[C:27]([OH:44])[C:28]4[C:40](=[O:41])[C:39]5[C:34](=[CH:35][CH:36]=[CH:37][C:38]=5[O:42][CH3:43])[C:32](=[O:33])[C:29]=4[C:30]([OH:31])=[C:25]3[CH2:24][C@@:23]([OH:49])([C:45]([CH2:47][OH:48])=[O:46])[CH2:22]2)[CH2:17][C@H:16]([NH2:50])[C@@H:15]1[OH:51].[C:1]([O-:11])(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 443939Doxorubicin HydrochlorideHCID 23665705Potassium 1,2,3,6-tetrahydro-2,6-dioxopyrimidine-4-carboxylate

Product 1

HCID 131727237HCID 131727237, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium orotate (0.4 g) synthesized in the above step was dissolved in 150 mL of water at 65° C. The solution was de-aired in vacuum and protected with argon. Doxorubicin hydrochloride (1.0 g, 1 eq) was added and the resulting red solution was treated with excess amount of amberlite IR120H resin for 2 hours at the same temperature. After filtration the solution was frozen in dry ice, and lyophilized to give 1.35 g of doxorubicin orotate (J-1220-13-II) as a red solid. Mass Spectroscopy (FIG. 3) and Nuclear Magnetic Resonance (FIG. 4) indicate that the structure is doxorubicin orotate.

Workup

  1. additionthe resulting red solution was treated with excess amount of amberlite IR120H resin for 2 hours at the same temperature
  2. filtrationAfter filtration the solution
  3. temperaturewas frozen in dry ice

Sources & evidence

ORD record
ord-491d3ceb879b4181a7c36d56f5e75129
Source dataset
uspto-grants-2012_04
Patent number
US08148339B2

Reaction notes

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