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Study On Synthesis Of D-α-aminoadipate And 1, 2-benzisothiazol-3(2H)-one

Posted on:2010-09-13Degree:MasterType:Thesis
Country:ChinaCandidate:C X MiaoFull Text:PDF
GTID:2121360275494072Subject:Physical chemistry
Abstract/Summary:PDF Full Text Request
We studied the synthesis of D-α-aminoadipate in the first section.The impotant applications ofα-aminoadipate and its derivatives in the field of pharmaceutical, pesticides and food are reviewed.And as a result of similar structure,the synthetic route of D-α-aminoadipate also applies to the development of D-glutamic acid, D-aspartic acid,etc.Pharmacological effects and clinical evaluation of amino acid and its derivatives were discussed briefly in the paper.Focused on the synthetic routes and synthetic conditions of D-α-aminoadipate.The parts are included as follows:1.We compared all the routes of the synthesis of D-α-aminoadipate in a great deal of literature.After thinking about the economic benefit,the environment problems and the feasibility in chemical production,adipic acid was used as the starting material to synthesize racemic D-α-aminoadipate by esterification,bromine replacing,esterification and hydrazining.The target compound was obtained by resolution with L-(-)-dibenzoyl-tartaric acid.2.We optimized the synthetic conditions of monoethyl adipate,and have solved the problem of low purity and low yield which greatly improved the product yield to 88.9%from 49.1%.3.The chiral reagent L-(-)-dibenzoyl-tartaric acid was successfully applied in chemical resolution of DL-α-aminoadipate,through related references and tests.A final product brought the enantiomeric purity up to 99.9%D with a yield of 68.9%.We studied the synthesis of 1,2-benzisothiazol-3(2H)-one in the second section. 1,2-benzisothiazol-3(2H)-one has an excellent performance of anti-bacterial,moldy and anti-corrosion.And as a green product,its toxicity is very small,will not cause cancer,mutations,and no harm to humans.Mainly used in the high-grade paint, pharmaceuticals and food.The impotant applications of 1,2-benzisothiazol-3(2H)-one and its derivatives in the field of pharmaceutical and food are reviewed.Focused on the synthetic routes and synthetic conditions of 1,2-benzisothiazol-3(2H)-one.The parts are included as follows: 1.We compared all the routes of the synthesis of 1,2-benzisothiazol-3(2H)-one in a great deal of literature.After thinking about the economic benefit,the environment problems and the feasibility in chemical production,anthranilic acid was used as the starting material to synthesize dithiosalicylic acid by diazo reaction.Then from dithiosalicylic acid to synthesis the target compound 1,2-benzisothiazol-3(2H)-one by two synthetic routes.2.We optimized the synthetic conditions of dithiosalicylic acid,and have solved the problem of low purity which greatly improved the product yield to 87%.3.We optimized the synthetic conditions of 1,2-benzisothiazol-3(2H)-one after researching the two synthetic routes.And the synthetic conditions that suites industrial technology were found out by ourselves.
Keywords/Search Tags:D-α-aminoadipate, synthetic routes, L-(-)-dibenzoyl-tartaric acid, chemical resolution, 1,2-benzisothiazol-3(2H)-one, green product, dithiosalicylic acid, industrial technology
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