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The Synthesis Research of Gemcitabine Hydrochloride

Author: ZhouJian
Tutor: LuoJun
School: Nanjing University of Technology and Engineering
Course: Pharmaceutical Engineering
Keywords: Gemcitabine Hydrochloride Anticancer drug Production Synthesis
CLC: TQ463.53
Type: Master's thesis
Year: 2011
Downloads: 190
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Abstract


Gemcitabine Hydrochloride, (+)-2’-deoxy-2’,2’-difluorocytidine monohydrochloride, is a new type anticancer drug and has played an important role in the treatment of various cancers. It was first developed by Eli Lilly Company. Clinical effective to:Non-small cell lung cancer、Pancreatic cancer、bladder cancer, breast cancer and any other solid tumors. This study was emphasized on looking for a suitable technical route for industrial production of Gemcitabine Hydrochloride.2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-l-methanesulfonate was used as starting materials. Bis(trimethylsilyl)cytosine was used for stereoselective glycosylation and the product was obtained via deprotection, salt formation and purification. The molar ratio of bis(trimethylsilyl)cytosine and the starting materials shoud be greater than 10, reaction temperature was between 115℃and 120℃, reaction time was 5～7 hours, and hexamethyl disilazane was found to be the superior solvent.β-difluoro cytidine was obtained by a yield higher than 99.0% under the above conditions. Methanol was used as the proper solvent in the deprotection process. Crude Gemcitabine hydrochloride was produced under the following conditions:pH should be controlled between 10 and 11, reaction temperature was 65℃, reaction time was 5～7 hours, then the pH value of result solution was adjusted between 2 and 3 in ethanol. Pure Gemcitabine hydrochloride was gotten with a purity of higher than 99.0% and total yield of 56.8% via decolorization in water by charcoal and concentration.The reaction mechanism was investigated and the resulting product was identified by FT/IR, H1-NMR, C13-NMR, MS and elemental analysis. The results Gemcitabine Hydrochloride was further confirmed by comparison analysis with authentic standard samples.This synthesizing methodology of Gemcitabine Hydrochloride was more suitable for commercial process.

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Production of organic compounds in drug > Heterocyclic compounds drugs > Five section heterocyclic
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