Pyridine → Doxorubicin

HRID 1009459Notes

Reaction equation

HRID 1009459 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][C@@H:15]1[O:20][C@@H:19]([O:21][C@@H:22]2[C:27]3=[C:28]([OH:45])[C:29]4[C:41](=[O:42])[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]=5[O:43][CH3:44])[C:33](=[O:34])[C:30]=4[C:31]([OH:32])=[C:26]3[CH2:25][C@@:24]([OH:50])([C:46]([CH2:48][OH:49])=[O:47])[CH2:23]2)[CH2:18][C@H:17]([NH2:51])[C@@H:16]1[OH:52].Cl>ClCCl>[CH3:14][C@@H:15]1[O:20][C@@H:19]([O:21][C@@H:22]2[C:27]3=[C:28]([OH:45])[C:29]4[C:41](=[O:42])[C:40]5[C:35](=[CH:36][CH:37]=[CH:38][C:39]=5[O:43][CH3:44])[C:33](=[O:34])[C:30]=4[C:31]([OH:32])=[C:26]3[CH2:25][C@@:24]([OH:50])([C:46]([CH2:48][OH:49])=[O:47])[CH2:23]2)[CH2:18][C@H:17]([NH2:51])[C@@H:16]1[OH:52]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 443939Doxorubicin Hydrochloride

Product 1

HCID 31703DoxorubicinYield 317.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in Example <1-1> (55 mg, 0.0168 mmol) and p-nitrophenylchloromate (94 mg, 0.047 mmol) were dissolved in 4 ml of dichloromethane, and pyridine (68 μl, 0.084 mmol) was added thereto, followed by stirring the mixture at room temperature for 2 days. After the reaction was completed, the reaction mixture was dried in a vacuum oven to remove the solvent and dissolved in N,N-dimethylformamide (3 ml), and triethylamine (14.2 μl, 0.1 mmol) and doxorubicin-hydrochloride (13.7 mg, 0.0235 mmol; Waco Pure Chemical Industries, Ltd.) were added thereto, followed the darkroom treatment of the resulting mixture with stirring at room temperature for 1 day. The resulting solution was concentrated, and the residue thus obtained was purified by column chromatography (dichloromethane:methanol=10:1), to obtain the title compound as a red sticky solid (40.5 mg).

Workup

  1. customthe reaction mixture was dried in a vacuum oven
  2. customto remove the solvent
  3. dissolutiondissolved in N,N-dimethylformamide (3 ml)
  4. stirringwith stirring at room temperature for 1 day
  5. concentrationThe resulting solution was concentrated
  6. customthe residue thus obtained
  7. customwas purified by column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-4a1c38c44a6b4f1290728a375bf62130
Source dataset
uspto-grants-2011_07
Patent number
US07973084B2

Reaction notes

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