ChemicalBook CAS DataBase List Epirubicin EP Impurity F

Epirubicin EP Impurity F synthesis

8synthesis methods

Product Name:Epirubicin EP Impurity F
CAS Number:57918-24-8
Molecular formula:C27H29NO10
Molecular Weight:527.53

9.0 g of the raw material was suspended in 460 mL of purified water. Then the temperature was cooled to 0 ~ 5 °C, and 60 mL of 3.5% sodium hydroxide solution was added dropwise for 50 minutes. After the reaction was complete, the pH was adjusted to 5.0 with hydrochloric acid. The reaction solution was subsequently washed twice with 200 mL of dichloromethane and the aqueous phase was collected. 1200 mL of dichloromethane and 80 mL of methanol were added to the aqueous phase, and the pH was adjusted to 8.2 with a 0.1 mol/L sodium hydroxide solution. Collect the organic phase. The organic phase was concentrated to dryness under reduced pressure Daunorubicin7.48g.
Epirubicin EP Impurity F

57918-22-6 Synthesis

(8S-cis)-8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-alpha-L-arabino-hexopyranosyl]oxy]naphthacene-5,12-dione

57918-22-6
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57918-24-8
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Yield:57918-24-8 98.3%

Reaction Conditions:

with sodium hydroxide in water monomer at 0 - 5; for 0.833333 h;

Steps:

26 Example 26 Preparation of Daunorubicin

9.0 g of the purified compound of the formula VIII was suspended in 460 mL of purified water.Cool down to 0 ~ 5 ° C,60 mL of 3.5% sodium hydroxide solution was added dropwise, and the reaction was kept for 50 minutes.After the reaction, the pH was adjusted to 5.0 with hydrochloric acid, washed twice with 200 mL of dichloromethane, and the aqueous phase was collected. 1200 mL of dichloromethane and 80 mL of methanol were added to the aqueous phase, and the pH was adjusted to 8.2 with a 0.1 mol/L sodium hydroxide solution. Dispose of the liquid and collect the organic phase.The organic phase was concentrated to dryness under reduced pressure Daunorubicin7.48g,The molar yield was 98.3%, the HPLC purity was 99.3%, and the maximum single impurity was 0.5%.

References:

CN109293613,2019,A Location in patent:Paragraph 0198; 0199

5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]-α-L-arabino-hexopyranosyl]oxy]-, (8S,10S)- (9CI)

73926-01-9
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57918-24-8
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References

26388-52-3 Synthesis

26388-52-3
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57918-24-8
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79441-78-4
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57918-24-8
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2H-Pyran-3(6H)-one, 6-methoxy-2-methyl-, (2S,6R)-

55102-46-0
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57918-24-8
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References