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Preparation method of aztreonam intermediate (3S-trans)-3-amido-4-methyl-2-oxo-1-sulfoazetidine

A technology of sulfonic nitrogen and tetracyclobutane, which is applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of low cost and few reaction steps, and achieve the effects of low cost, many reaction steps and easy availability of raw materials

Active Publication Date: 2010-02-03
CHONGQING LUMMY PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In summary, there is no (3S-trans)-3-amino-4-methyl-2-oxo-1-sulfonic acid nitrogen with few reaction steps, low cost and suitable for large-scale production in the market. The preparation method of heterocyclobutane

Method used

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  • Preparation method of aztreonam intermediate (3S-trans)-3-amido-4-methyl-2-oxo-1-sulfoazetidine

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preparation example Construction

[0028] The preparation of embodiment one N-benzyloxycarbonyl-L-threonine

[0029]

[0030] 60 g (0.5 mol) of L-threonine was put into the reaction flask, 200 ml of 12% NaOH solution was added, cooled to 0° C. in an ice bath, 78 g (0.6 mol) of benzyloxycarbonyl chloride was added dropwise, and stirred at room temperature for 5 hours after the dropwise addition was completed. After the reaction is completed, add 30% HCl, adjust the pH to 8-9, wash with ethyl acetate, add the reaction solution and cool it down to 0-5°C, add concentrated hydrochloric acid to acidify, stir and crystallize at pH ≤ 1, filter, and dry to obtain Target product 97.8g.

[0031] MS: m / z: 263.

[0032] Elemental analysis data: C: 56.98%; H: 5.91%; N: 5.55%; O: 31.56%.

Embodiment 2

[0033] The preparation of embodiment two (2S, 3R)-2-(benzyloxycarbonyl-amino)-3-hydroxybutanamide

[0034]

Embodiment 1

[0035] 76 g (0.3 mol) of N-benzyloxycarbonyl-L-threonine prepared in Example 1 was put into a reaction flask, 200 ml of methanol was added, ammonia gas was slowly introduced, the reaction was stirred for 8 hours, the reaction was stopped, and ethyl acetate was recrystallized to obtain Target product 71.3 g.

[0036] MS: m / z: 262.

[0037] Elemental analysis data: C: 57.42%; H: 5.88%; N: 11.22%; O: 25.48%.

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Abstract

The invention relates to a method for preparing (3S-trans)-3-amino-4-methyl-2-oxoazetidine-1-azetidinesulfonic acid, belonging to the field of chemical synthesis medicines. The preparation method hassimple steps and low cost, and is characterized in that: a. N-R1-L-threonine is dissolved in an anhydrous polar solvent and then ammonia is introduced for reaction, so as to obtain (2S, 3R)-2-(R1-amino)-3-hydroxyl butyramide; R1 is a protection group of amino; b. after the product of the step a is dissolved in methanol, strong acid ion exchange resin containing sulfonic acid groups is added in andthen SO3 gas is introduced for reaction, so as to obtain the (3S-trans)-3-(R1-amino)-2-methyl-4-oxoazetidine-1-azetidinesulfonic acid; the weight ratio of the (2S, 3R)-2-(R1-amino)-3-hydroxyl butyramide and the strong acid ion exchange resin is 1:1.8 to 1:3.5; c. the (3S-trans)-3-amino-4-methyl-2-oxoazetidine-1-azetidinesulfonic acid can be obtained by removing the protection group of amino of the product of the step b.

Description

technical field [0001] The invention relates to a preparation method of (3S-trans)-3-amino-4-methyl-2-oxo-1-sulfonic acid azetidine, which belongs to the field of chemical synthesis medicine. Background technique [0002] Aztreonam is a monocyclic β-lactam antibiotic with the chemical name [2S-[2α,3β(Z)]]-2-[[[1-(2-amino-4-thiazolyl)-2-[ (2-Methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylene]amino]oxo]-2-methylpropionic acid, which Structure is as shown in formula I: [0003] [0004] Aztreonam was launched in Italy in 1984, and it was the first monocyclic β-lactam antibiotic applied to the market. Aztreonam has a broad antibacterial spectrum and has high antibacterial activity against most aerobic Gram-negative bacteria, including Escherichia coli, Klebsiella pneumoniae and Oxitobacter, aerogenes, cloacae, proteus Bacteria, Serratia, Citrobacter, Shigella and other Enterobacteriaceae bacteria, as well as influenza bacillus, Neisseria gonorrhoeae, meningococcus, etc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D205/08
CPCY02P20/55
Inventor 彭建坤邱宇赵新祥王玲
Owner CHONGQING LUMMY PHARMA