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Synthesis method of fosaprepitant dimeglumine

A technology for fosaprepitant dimeglumine and a synthesis method, applied in the field of medicine, can solve the problems of inability to purify, unstable in nature, easy to decompose, etc., and achieves mild and controllable reaction conditions, easily available raw materials, and high yield. Effect

Inactive Publication Date: 2013-07-17
SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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Problems solved by technology

[0006] The bisbenzyl ester in this process is a viscous liquid that cannot be purified, and is unstable and easy to decompose, so it is not suitable for storage as an intermediate in the production process

Method used

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  • Synthesis method of fosaprepitant dimeglumine
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  • Synthesis method of fosaprepitant dimeglumine

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Embodiment Construction

[0022] The technical solutions of the present invention will be described in detail below in conjunction with specific embodiments. Herein, the exemplary embodiments and descriptions of the present invention are used to explain the technical solutions of the present invention, but are not intended to limit the present invention.

[0023] Fosaprepitant dimeglumine synthetic method comprises the following steps: the general route of reaction is:

[0024]

[0025] The first step: the preparation process of the starting material aprepitant (SM001):

[0026] 1. The synthesis of (R)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl-1-alcohol, the operation steps include:

[0027] (1) Dissolve 350mL methyl sulfide borane and 120mL (s)-CBS in 2.5L methyl tert-butyl ether and cool to -5°C.

[0028] (2) 1.5kg of 3,5-bis(trifluoromethyl)acetophenone was dissolved in 5L of methyl tert-butyl ether, and slowly dropped into the above system.

[0029] (3) After the dropwise addition, continue to s...

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Abstract

The invention relates to the field of medicaments, and in particular provides a synthesis method of fosaprepitant dimeglumine. According to the method of the invention, aprepitant is employed as initial material to be reacted with tetrabenzyl pyrophosphate in anhydrous tetrahydrofuran with sodium hexamethyldisilazide as a base to obtain dibenzyl ester intermediate, a benzyl group of the dibenzyl ester is removed in anhydrous methanol to generate single-benzyl ester intermediate, which is hydrogenated to remove a remaining benzyl group, and salified with meglumine to obtain fosaprepitant dimeglumine. The method comprises three major steps: (1) preparing intermediate S100902; (2) preparing crude fosaprepitant dimeglumine; and (3) refining crude fosaprepitant dimeglumine. The synthesis method is featured as abundant available raw materials, moderate and controllable reaction conditions, simple process, high yield and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicine and discloses a method for synthesizing fosaprepitant dimeglumine. Background technique [0002] Fosaprepitant dimeglumine, the Chinese chemical name is deoxy-1-(methylamino)-D-sorbitol[3-[[(2R,3S)-2-[(1R)-1-[3,5 -Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-2,5-dihydro-5-oxo-1H- 1,2,4-triazol-1-yl]phosphate (2:1), the molecular formula is C 23 h 22 f 7 N 4 o 6 P·2C 7 h 17 NO 5 , molecular weight 1004.83, white to off-white powder, odorless, hygroscopic, easily soluble in methanol and water, very slightly soluble in absolute ethanol, specific rotation +28°~+33°, mainly used for To treat nausea and vomiting caused by chemotherapy. [0003] In the prior art, the synthetic method of fosaprepitant dimeglumine has following several kinds: [0004] 1. The document J.Med.Chem.2000, 43.1234-1241 reported that aprepitant reacted with tetrabenzyl pyrophosphate under the acti...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C07C215/10C07C213/08
Inventor 李明杰李强林相菊罗兆亮
Owner SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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