Preparation method of 1-(4, 5-dihydro-2-thiazolinyl)-3-mercaptoazetidine hydrochloride

A technology based on mercaptoazetidine hydrochloride and thiazoline, applied in the new preparation field of 1--3-mercaptoazetidine hydrochloride, can solve the problems of long route, harsh reaction conditions, high cost, etc. The route is simple, the raw materials are easy to obtain, and the effect of increasing the yield
CN102250080AActive Publication Date: 2011-11-23GUANGZHOU BAIYUNSHAN PHARMA HLDG CO LTD BAIYUNSHAN PHARMA GENERAL FACTORY
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
GUANGZHOU BAIYUNSHAN PHARMA HLDG CO LTD BAIYUNSHAN PHARMA GENERAL FACTORY
Publication Date
2011-11-23

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Abstract

The invention discloses a method for synthesis of 1-(4, 5-dihydro-2-thiazolinyl)-3-mercaptoazetidine hydrochloride. With 2-methylthio-2-thiazoline (I) as the raw material, the method of the invention comprises the steps of: in the presence of alkali, reacting 2-methylthio-2-thiazoline (I) with 3-hydroxyazetidine hydrochloride so as to obtain 1-(4, 5-dihydro-2-thiazolinyl)-3-hydroxyazetidine (II), and reacting (II) with methyl sulfonylchloride in the presence of alkali so as to obtain 1-(4, 5-dihydro-2-thiazolinyl)-3-methane sulfonate group azetidine (III), subjecting (III) to a reaction with potassium thioacetate so as to obtain 1-(4, 5-dihydro-2-thiazolinyl)-3-thioacetic acid ester group azetidine (IV), in the presence of alkali, subjecting (IV) to hydrolysis and then to acidification with dilute hydrochloric acid, thus obtaining the 1-(4, 5-dihydro-2-thiazolinyl)-3-mercaptoazetidine hydrochloride (V). With easily available and inexpensive starting material, the method of the invention simplifies the synthesis route, improves the raw material utilization ratio and the overall yield. An intermediate obtained in the reaction can be subjected to refinement by a recrystallization method or to a next reaction directly, so that the yield is high and the "three wastes" produced during the reaction process are few. In addition, with low cost, the method of the invention is beneficial for industrial production.
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Description

technical field

[0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a new preparation method of 1-(4,5-dihydro-2-thiazolinyl)-3-mercaptoazetidine hydrochloride. Background technique

[0002] The present invention relates to the preparation of the key intermediate 1-(4,5-dihydro-2-thiazolinyl)-3-mercaptoazetidine hydrochloride (V) of the novel antibacterial drug tipipenem pivoxil (VI) Synthetic, the structural formula is as follows:

[0003]

[0004] Tebipenem pivoxil (Tebipenem pivoxil) is a new broad-spectrum antibiotic (VI) of oral penem class, originally developed by Wyeth Rieter Co., Ltd. of Japan, and then transferred to Meiji Seika Pharmaceutical Co., Ltd. of Japan in March 2002. In 2009 It was approved by the Ministry of Health and Welfare in Japan in April, and it was first listed in Japan on August 26, 2009. Tipipenem pivoxil has a broad antibacterial spectrum. For most clinically isolated strains, tipipenem pivoxil ha...

Claims

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