Daunorubicin Hydrochloride → HCID 14139407, compound

HRID 620906Notes

Reaction equation

HRID 620906 reaction equation
C[C@@H]1O[C@@H](O[C@@H:9]2[C:18]3[C:13](=[C:14]([OH:32])[C:15]4[C:24](=[O:25])[C:23]5[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=5[C:20](=O)[C:16]=4[C:17]=3[OH:19])[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)C[C@H](N)[C@@H]1O.Cl.[H][H]>CO.[Pd]>[C:33]([C@:11]1([OH:36])[CH2:12][C:13]2[C:14](=[O:32])[C:15]3[C:24]([OH:25])=[C:23]4[C:22]([C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26]4)=[CH:20][C:16]=3[C:17](=[O:19])[C:18]=2[CH2:9][CH2:10]1)(=[O:34])[CH3:35]

Participants

5

Reactant 2

HCID 62770Daunorubicin Hydrochloride2×HCID 178418361HCID 178418361, compound

Product 1

HCID 14139407HCID 14139407, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Daunomycin hydrochloride (compound 17) (20 mg) in dry methanol (20 ml) was catalytically reduced with hydrogen gas and 5% palladium on barium sulfate (20 mg) 5.5 h at room temperature. Exposure of the mixture to the atmosphere gave a red solution which was filtered, evaporated and preparatively chromatographed on silica gel layers using chloroform/methanol (98:2) as eluant. The red band Rf 0.28-0.43 gave the product (compound 19) as a red solid (12 mg, 88%).

Workup

  1. customExposure of the mixture to the atmosphere gave a red solution which
  2. filtrationwas filtered
  3. customevaporated
  4. custompreparatively chromatographed on silica gel layers

Sources & evidence

ORD record
ord-0c0e6f273bc24d88a2d6b41e64c21778
Source dataset
uspto-grants-1989_04
Patent number
US04822873

Reaction notes

Loading…