Synthetic method of (2S, 3S)-2-[(carbamoyloxy) methyl]-3-amido-4-oxoazetidinone-1-sulfonate

A technology of aminocarbonyloxymethyl and acridinone, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of long route, low total yield, expensive reagents, etc., and achieve the effect of simplifying the reaction steps and increasing the yield

Active Publication Date: 2008-11-05
上海立科化学科技有限公司
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  • Abstract
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Problems solved by technology

[0005] The method route described in the literature is too long, the reaction is unstable, the total yield is on the low side (<1%), and quite a lot of reagents are expensive, so it is not suitable for industrialized production

Method used

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  • Synthetic method of (2S, 3S)-2-[(carbamoyloxy) methyl]-3-amido-4-oxoazetidinone-1-sulfonate

Examples

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Embodiment Construction

[0030] Below in conjunction with specific embodiment further illustrate how the present invention is realized:

[0031] step one:

[0032] In a 1000mL three-necked flask, add 133g of L-aspartic acid and dissolve in dichloromethane, add 3g of red phosphorus, and dropwise add Br 2 240g, the molar ratio of L-aspartic acid to bromine is 1:1.5, keep the temperature at 0-10°C, after the dropwise addition is completed, heat to 50°C for reaction, follow the HPLC until the reaction is complete, distill off the dichloromethane, add After dissolving in 1000mL water, 10% NaOH solution was added dropwise to adjust the pH value to 3-3.5, and the product was precipitated to obtain the product (2R, 3R)-2-bromo-3-aminosuccinic acid, which was dried to obtain 200g, with a purity of 98%, yield 92%.

[0033] Step two:

[0034] Dissolve 212g (2R, 3R)-2-bromo-3-aminosuccinic acid in 1000mL of methanol, if it cannot be dissolved, add 158g of pyridine, heat to 40°C, slowly add 238g of thionyl chl...

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Abstract

The invention relates to a synthetic method of (2S, 3S)-2-[(carbamoyloxy) methyl]-3-amino-4-oxoazetidinone-1-sulfonate which includes the following steps: step one: dropping bromine into a solvent containing L-aspartic acid and obtaining (2R, 3R)-2-bromine-3-amino-succinic acid under the catalyzing of red phosphorus; step two: dropping thionyl chloride into the solvent containing naphthyridine for closed loop esterification; step three: using sodium azide to carry out heating reaction with (2R, 3R)-3-bromine-4-oxoazetidinone-2-methyl formate in the solvent; step four: using sodium borohydride to reduce (2R, 3S)-3-azide-4-oxoazetidinone-2-methyl formate in the solvent; step five: using chlorosulfonyl isocyanate to react with (3S, 4S)-3-azide-4- hydroxymethyl-2-azetidinone in the solvent; step six: using sulfur trioxide pyridine to completely react with (2S, 3S)-3-azide-4-oxoazetidinone-2-methyl carbamate in the solvent; step seven: obtaining the (2S, 3S)-2-[(carbamoyloxy) methyl]-3-amino-4- oxoazetidinone-1-sulfonate by Pd / C catalyzing and hydrogenation in the solvent.

Description

technical field [0001] The invention relates to the synthesis of pharmaceutical intermediates, in particular to a synthesis method of (2S, 3S)-2-aminocarbonyloxymethyl-3-amino-4-acridinone-1-sulfonic acid. Background technique [0002] The sulfonic acid shown in compound 1 is a key intermediate in the synthesis of the antibiotic drug carumonam (Carumonam), which is prepared from L-aspartic acid, namely compound 2, through a six-step reaction. [0003] [0004] It has been reported that compound 1 was obtained by using ascorbic acid (Vc) as a starting material through 12 steps, and there was also a report in the literature that compound 1 was obtained by using (D)-tartaric acid as a starting material through 15 steps. [0005] The method described in the literature is too long, the reaction is unstable, the total yield is low (<1%), and quite a lot of reagents are expensive, so it is not suitable for industrial production. Contents of the invention [0006] The techn...

Claims

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Application Information

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IPC IPC(8): C07D205/085C07B53/00
Inventor 张芳江
Owner 上海立科化学科技有限公司
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