Method for preparing N-tert-butyloxycarbonyl-3-hydroxy-1-adamantyl-d-glycine

A technology of adamantylglycine and tert-butoxycarbonyl, which is applied in the field of preparation of N-tert-butoxycarbonyl-3-hydroxy-1-adamantylglycine, can solve the problems of difficult preparation and preservation of biological enzymes, and achieves Solve the effect of difficult preparation and preservation, lower production cost and high yield

Inactive Publication Date: 2014-10-15
天津民祥生物医药股份有限公司
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Problems solved by technology

[0008] In the prior art, from compound 5 [2-(3-hydroxyl-1-adamantyl)-2-1-oxoacetic acid (3)] to compound 6 (3-hydroxyl-1-adamantane glycine) to pass Biological enzymes are split, because biological enzymes are not easy to prepare and preserve, so it is necessary to seek an alternative method to carry out the preparation of saxagliptin intermediates, that is, the compound 5[2-(3-hydroxyl-1-adamantine The reaction process of alkyl)-2-1-oxoacetic acid (3)] to compound 7 (N-tert-butoxycarbonyl-3-hydroxyl-1-adamantylglycine)

Method used

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  • Method for preparing N-tert-butyloxycarbonyl-3-hydroxy-1-adamantyl-d-glycine
  • Method for preparing N-tert-butyloxycarbonyl-3-hydroxy-1-adamantyl-d-glycine
  • Method for preparing N-tert-butyloxycarbonyl-3-hydroxy-1-adamantyl-d-glycine

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Embodiment

[0032] A preparation method of N-tert-butoxycarbonyl-3-hydroxyl-1-adamantylglycine, the compound 5[2-(3-hydroxyl-1-adamantyl)-2-1- The reaction process of oxoacetic acid (3)] to compound 7 (N-tert-butoxycarbonyl-3-hydroxyl-1-adamantylglycine) is carried out by replacing the reaction process of compound A to G in the following steps:

[0033](1) Put 130ml of absolute ethanol into a three-necked flask, cool it in an ice-salt bath to below -5°C, slowly add thionyl chloride (8ml, 110mmol) dropwise, and control the temperature not to exceed -5°C during the dropwise addition; After the addition was completed, compound A (20 g, 89 mmol) was added in batches, and the temperature was controlled to be lower than -5°C during the addition; after the addition was completed, the reaction solution was stirred at room temperature for 5 h, then the reaction solution was concentrated to 50 ml, and cooled to Below 0°C, add 100ml of toluene and 20g of triethylamine respectively; the reaction solu...

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Abstract

The invention discloses a method for preparing N-tert-butyloxycarbonyl-3-hydroxy-1-adamantyl-d-glycine. A chemical synthesis method is adopted to replace preparation of a saxagliptin intermediate in the prior art, a chiral inducer participates in a reaction to perform chiral synthesis, and the preparation method is simple and convenient to operate and high in yield, reduces production cost of the intermediate and solves the technical problem of difficulty in biological enzyme preparation and storage caused by the fact that resolution needs to be performed through biological enzymes in the prior art.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to a preparation method of N-tert-butoxycarbonyl-3-hydroxyl-1-adamantylglycine. Background technique [0002] Saxagliptin, an incretin-based hypoglycemic drug jointly developed by two global pharmaceutical companies, Bristol-Myers Squibb and AstraZeneca, has been launched in many countries including the United States, India and the European Union. 46 countries within the country have obtained marketing approval. Saxagliptin, a potent dipeptidyl peptidase-4 inhibitor, is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes. [0003] In May 2011, it was officially approved by SFDA in China. The drug can be used as a monotherapy, or in combination with metformin on the basis of poor control of metformin. Clinical studies have confirmed that saxagliptin has the advantages of outstanding curative effect and long-lasting effect. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/22
Inventor 张杰刘万里薛志杰曹晖李金娜陈瑞香宋建民
Owner 天津民祥生物医药股份有限公司
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