Chloroform → Adriamycin aglycone

HRID 596933Notes

Reaction equation

HRID 596933 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:11]3[C:22]([OH:23])=[C:21]4[C:16]([CH2:17][C@@:18]([OH:29])([C:25]([CH2:27]Br)=[O:26])[CH2:19][C@@H:20]4[OH:24])=[C:15]([OH:30])[C:12]=3[C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:10].C(Cl)(Cl)Cl.[OH-:35].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:11]3[C:22]([OH:23])=[C:21]4[C:16]([CH2:17][C@@:18]([OH:29])([C:25]([CH2:27][OH:35])=[O:26])[CH2:19][C@@H:20]4[OH:24])=[C:15]([OH:30])[C:12]=3[C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:10]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 1120236914-Bromodaunomycinone

Product 1

HCID 72401Adriamycin aglycone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In order to introduce a hydroxyl group at the 14- position of compound (IX), said position is first provided with a bromine atom in conventional bromination step (Br2, CHCl3, 23°, 16 hrs). The 14-bromodaunomycinone (X), after being freed of CHCl3, is dissolved in aqueous acetone and subjected to hydrolysis with NaOH (1.1 eq, reflux 5 mins) to afford adriamycinone (XI) which is recovered after water workup and extraction with CHCl3 /MeOH. This portion of the process forms the subject of Example 7. ##STR4##

Sources & evidence

ORD record
ord-1da059cfba504849b2a08c3d1e8bf1ae
Source dataset
uspto-grants-1977_03
Patent number
US04012448

Reaction notes

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