Doxorubicin Hydrochloride → HCID 131727237, compound

HRID 2377566Notes

Reaction equation

HRID 2377566 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 650 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 IR120 H 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 IR120 H resin for 2 hours at the same temperature
  2. filtrationAfter filtration the solution
  3. temperaturewas frozen in dry ice

Sources & evidence

ORD record
ord-9f755dc1a449414d948f2345257f419e
Source dataset
uspto-grants-2008_12
Patent number
US07470672B2

Reaction notes

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