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The Asymmetric Synthesis of 3-Tetrahydrofuran Acid、the Synthesis of Dozolamide Intermediate and the Optimization of the Functional Organic Molecule Synthesis

Author: QiHaoQiang
Tutor: HuWenHao
School: East China Normal University
Course: Organic Chemistry
Keywords: 3-tetrahydrofuran acid Glaucoma Dozolamide Anginal Ivabradine
CLC: TQ463.5
Type: Master's thesis
Year: 2009
Downloads: 258
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Abstract


The structure of Furan acid is the important molecular skeleton,such as the 2-tetrahydrofuran acid structure of Faropenem.Recent years,People start to study the molecular structure of 3-tetrahydrofuran acid or some moleculars which act as precursors in some complex structure compounds,and study the biology influence of this configuration.However,few people reported the asymmetric synthesis of 3-tetrahydrofuran acid,the highest ee value which is reported was 23%.We have found one way that can asymmetrily synthesize the 3-tetrahydrofuran acid through asymmetric resolution,the separation of diastereoisomers and the homogenous catalyst hydrogenation reaction.The best result is 99%ee.We reported the asymmetric synthesis of this small compound for the first time.The synthesis route of dozolamide intermediate is designed.From acetylacetic ester,by the Sodium borohydride reduction,the SN2 reaction by 2-mercapotthiophene,hydrolysis by acid,the Friedel -Crafts acylation reaction,sulfonic amide reaction and oxidation by the metachloroperbenzoic acid,the intermediate of dozolamide is synthesized by these seven reactions.The total yield is 16.4%.The raw materials of this synthesis route are all available from commercial channel.The target compound of this synthesis route is not reported by anyone and not available in the commercial way.This route has the potential value of process.In the condition of Raney Ni,60℃,10atm H2,4 Hrs,the compound which acts as an important intermediate of Ivabradinehydrochlorid which treats anginal is synthesized.The synthesis process of this intermediate is simplied and the target compound can be obtained by the economic way.The traditional way of the synthesis of 3-aza-4-oxo-tricyclo[4.2.1.0（2,5）]non -7-ene used strong base,but the yield was low.The weak base such as Tri-Sodium Phosphate Dodecahydrate,sodium carbonate and sodium dicarbonate can be used to double the yield of target compound successfully.And then this method can simplify the reaction and obtain the target compound by one reaction.

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