ChemicalBook CAS DataBase List Daunorubicin hydrochloride

Daunorubicin hydrochloride synthesis

8synthesis methods

Product Name:Daunorubicin hydrochloride
CAS Number:23541-50-6
Molecular formula:C27H30ClNO10
Molecular Weight:563.98

5,12-Naphthacenedione, 7,7'-[methylenebis[[(3aS,4S,6R,7aS)-tetrahydro-4-methyl-2H-pyrano[4,3-d]oxazole-1,6(6H)-diyl]oxy]]bis[9-acetyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-, (7S,7'S,9S,9'S)-

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Yield:-

Reaction Conditions:

Stage #1: daunoform in dimethylsulfoxide-d6;water-d2; for 24 h;
Stage #2: with hydrogenchloride in dimethylsulfoxide-d6;water-d2;

Steps:

6; 7

Crystalline dimeric formaldehyde conjugate of daunorubicin (2.8 mg, 2.6 μmol) was dissolved in 500 μL of DMSO-d₆(stored over 3 A molecular sieves) and analyzed by 400 MHz, ¹H NMR. NMR analysis showed that the dimeric formaldehyde conjugate of daunorubicin was stable in DMSO for at least 14 h. Upon addition of 25 μL of D₂O to the 500 μL DMSO-d₆sample, the dimeric formaldehyde conjugate of daunorubicin reacted over a 24 h period to form an equilibrium mixture consisting of 67% dimeric formaldehyde conjugate of daunorubicin and 32% of an intermediate. Because of the complexity of the spectrum, a structure could not be assigned to the intermediate; however, the intermediate appeared to have an oxazolidine ring. Upon addition of 3 equiv of hydrochloric acid in 130 μL of deuterium oxide, hydrolysis to daunorubicin-HCl was complete. The hydrochloric acid solution was prepared by the addition of 10 μL of concentrated HCl to 990 μL of D₂O. The formaldehyde released from the dimeric formaldehyde conjugate of daunorubicin was detected as its hydrate. The final product was identified as daunorubicin by comparison of the NMR spectrum with that of a sample of daunorubicin plus 3 equiv of HCl. Further, the final product was isolated by removal of all volatile components under vacuum (0.1 Torr), and its ¹H NMR spectrum was identical to that of daunorubicin-HCl.

References:

US6677309,2004,B1 Location in patent:Page/Page column 17; 18; 56