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Synthesis Study of a Key Intermediate of Atorvastatin Calcium Side-chain and Chiral Separation of β-amino Acid Derivatives by HPLC

Author: DongDongYin
Tutor: YangPing
School: East China Normal University
Course: Organic Chemistry
Keywords: Atorvastatin calcium Synthesis High performance liquid β-amino acid derivatives Chiral separation
CLC: TQ463.2
Type: Master's thesis
Year: 2009
Downloads: 307
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Abstract


The content of this paper is divided into two parts: the alpha statin the calcium side chain intermediate synthesis research and β - amino acid derivatives by high performance liquid chromatography chiral separation . Atorvastatin calcium is a new generation of the hydroxymethyl glutaryl phthalocyanine coenzyme A (HMG CoA) reductase inhibitors (statins Antihyperlipidemics ) . It can lower cholesterol , as well as lower diacylglycerol vinegar role than the other statins . Its efficacy , fewer side effects , hold a dominant position in the market of lipid-lowering drugs , the pace of development is also the forefront of statins . Statins Synthesis Usually by the convergent method , i.e. first single synthesis of the parent ring and having a chiral bis hydroxy hexanoate , and then condensation to obtain a final product . Reported on the synthesis of the side chain , literature . We have studied (2R, 4S) -4 - chloro -6 - iodomethyl -2,2 - dimethyl - [1,3] - Synthesis of dioxane , therefrom can easily be further converted into a prepared statin intermediates , after a study of the existing synthetic route , we proposed an innovative line : cheap ( R ) - epichlorohydrin as starting material offensive epoxy vinyl Grignard reagent open-loop , (Boc) 2 O protection Iodolactonization acetone fork and then through the protection of the target product . The method via a chiral source induced another chiral center , compared to other methods , to avoid the pollution of the heavy metal , and can be well to keep a first chiral chiral center . The other part is the use of high performance liquid chromatography chiral separation of β - amino acid derivatives . By high performance liquid chromatography in the past 20 years , tremendous progress has been made in the optical resolution of enantiomers indeed feasible method for the determination of optical purity and optically pure drugs . In this thesis, amylose chiral separation conditions of exploration the triphenyl ester chiral stationary phases first 4 - β- amino derivatives , mainly to discuss the mobile phase species , pH modifiers and flow rate on the retention and demolition points of impact , and ultimately get the better chiral separation conditions . Using the chiral separation of the condition can be easily detected by a variety of β-amino acid derivatives in a relatively short period of time , .

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Production of organic compounds in drug > Aliphatic compounds, drugs
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