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Preparation method of 2-oxothiopropionamide

A technology of oxothiopropionamide and thiol, which is applied in the field of preparation of 2-oxothiopropionamide, can solve the problems of difficult industrialization, difficult industrialization, high toxicity and the like

Active Publication Date: 2019-12-27
SHANGHAI INST OF PHARMA IND +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] There are big problems in this route. First, the preparation of acetone cyanide requires the use of cyano reagents, which are highly toxic; the highly toxic gas hydrogen sulfide is bubbled overnight, making it difficult to industrialize; the post-processing also requires the use of column chromatography, which also makes industrialization difficult. larger

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  • Preparation method of 2-oxothiopropionamide
  • Preparation method of 2-oxothiopropionamide
  • Preparation method of 2-oxothiopropionamide

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[0034] The preparation method of the present invention overcomes the disadvantages of using highly toxic cyano reagent, highly toxic gas hydrogen sulfide, silica gel column chromatography, etc. in the existing method for preparing 2-oxothiopropionamide, and provides a A kind of preparation method of 2-oxothiopropionamide completely different from prior art.

[0035] The preparation method of the present invention comprises the steps of preparing 2-oxopropionamide from ethyl 2-oxopropionate in ammonia methanol solution, and further obtaining 2-oxothiopropionamide through sulfuration of phosphorus pentasulfide.

[0036] Compared with the literature method, the preparation method of the present invention uses safe, cheap and easy-to-obtain ethyl pyruvate, ammonia methanol solution and phosphorus pentasulfide to replace the highly toxic cyano reagent and hydrogen sulfide in the original research route, and avoids column chromatography The use is easy to realize industrial producti...

Embodiment 1

[0065] Embodiment 1: the preparation of 2-oxopropanamide

[0066] Slowly add 50g of ethyl pyruvate (430.8mmol, 1eq) dropwise into 250ml of 7M methanol solution of ammonia at 0°C, stir at 0°C for 30min, a white solid precipitates, is suction filtered, and dried at room temperature to obtain 36.8g of a white solid, yield 98.3%. [M+H] + =88, 1 HNMR (CDCl 3 , 400MHz) δ: 2.72 (s, 3H, CH3), the purity is higher than 98%.

Embodiment 2

[0067] Embodiment 2: the preparation of 2-oxopropanamide

[0068] Slowly add 50g of ethyl pyruvate (430.8mmol, 1eq) dropwise to 250ml of 7M methanol solution of ammonia at room temperature, stir at 0°C for 30min, a white solid precipitates, is suction filtered, and dried at room temperature to obtain 32.3g of white solid, yield 86.4 %. [M+H] + =88, the purity is higher than 98%.

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Abstract

The invention relates to a preparation method of 2-oxothiopropionamide. Specifically, the invention discloses a preparation method of an intermediate compound used for preparing Lanabecestat. The method is simpler and safer in reaction and suitable for industrialization.

Description

technical field [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, and in particular relates to a preparation method of 2-oxothiopropionamide. Background technique [0002] Lanabecestat is a β-amyloid precursor protein cleavage enzyme 1 (BACE1) inhibitor developed by AstraZeneca for prodromal or mild Alzheimer's disease, and is currently in phase III clinical trials. In the previous phase I study, the discovery phase can significantly and dose-dependently reduce the level of β-amyloid in the brains of patients and healthy subjects, and it was found to have a long-term effect, which is the only one with a long-term effect found so far. BACE inhibitors. The FDA has granted Lanabecestat a Fast Track designation for its AD clinical development project. [0003] The structural formula of Lanabecestat is as follows: [0004] [0005] The existing synthetic route of Lanabecestat is as follows (reference: CN103380133A): [0006] The key in...

Claims

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Application Information

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IPC IPC(8): C07C327/42C07C231/02C07C235/74
CPCC07C231/02C07C327/42C07C235/74
Inventor 张鹏蔡正艳
Owner SHANGHAI INST OF PHARMA IND
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