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Method for purifying 2, 2-dimethyl-cyclopropane carboxamide produced by biocatalytic method

A technology of dimethylcyclopropane carboxamide, biocatalysis method, applied in microorganism-based methods, biochemical equipment and methods, carboxylic acid amide separation/purification, etc., can solve the problem of difficult to meet industrial production, product recovery rate and purity Low problems, to achieve the effect of simple and easy production process, high product recovery rate and easy industrial production

Active Publication Date: 2009-06-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The superiority of these enzymatic conversion methods demonstrates its good industrial application prospects, but the product recovery rate and purity are low, and it is difficult to meet the requirements of industrial production

Method used

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  • Method for purifying 2, 2-dimethyl-cyclopropane carboxamide produced by biocatalytic method
  • Method for purifying 2, 2-dimethyl-cyclopropane carboxamide produced by biocatalytic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Inoculate the Delftia tsuruhalensis CCTCC No.M 205115 activated by the slant into a 1L Erlenmeyer flask containing 200ml of seed medium, and prepare the seed medium per 1000mL as follows: mannitol 10.0g, yeast extract 5.0g, peptone 2.0 g, NaCl1.0g, K 2 HPO 4 1.0g, KH 2 PO 4 1.0g, MgSO 4 0.2g, FeSO4 0.01g, CaCl 2 0.05g, made up to 1000mL with water, natural pH (121°C, sterilized for 20min), cultured at 0°C for 20h, to obtain seed liquid.

[0020] The above seed solution was inoculated into a 5L fermenter filled with 70% fermentation medium. The fermentation medium is prepared as follows per 1000mL: glucose 10.0g, yeast extract 5.0g, peptone 2.0g, NaCl 1.0g, K 2 HPO 4 1.0g, KH 2 PO 4 1.0g, MgSO 4 0.2g, FeSO 4 0.01g, CaCl 20.05g, caprolactam 1.0g, make up to 1000mL with water, pH7.0 (sterilized by solid tank). Under the conditions of aeration rate of 1:0.5 (ratio of the volume of the culture solution to the volume of air introduced per minute), stirring...

Embodiment 2

[0023] Inoculate the strain Rhodococcus equi CCTCC No.M 205114 activated on the slant into a 1L Erlenmeyer flask containing 200ml of seed medium, and prepare the seed medium per 1000mL as follows: glucose 14.0g, yeast extract 5.0g, NaCl 1.0g , K 2 HPO 4 1.0g, KH 2 PO 4 1.0g, MgSO 4 0.2g, FeSO4 0.01g, CoCl 2 0.01g, CaCl 2 0.05g, made up to 1000mL with distilled water, natural pH (121°C, sterilized for 20min), cultured at 30°C for 2 days to obtain seed liquid.

[0024] Inoculate the above seed solution into a 10L fermenter with 5L of fermentation medium, and prepare the following composition per 1000mL of fermentation medium: glucose 20.0g, yeast extract 5.0g, urea 6.0g, NaCl 1.0g, K 2 HPO 4 1.0g, KH 2 PO 4 1.0g, MgSO 4 0.2g, FeSO4 0.01g, CoCl 2 0.01g, CaCl 2 0.05g, caprolactam 3.0g, distilled water to make up to 1000mL, pH natural (solid tank sterilization). Cultivate for 60 hours at a ventilation rate of 1:0.8, a stirring speed of 280 rpm, a tank pressur...

Embodiment 3

[0027] Each get 0.5L of the conversion liquid obtained in Example 1 or 2, and process it in the following solid-liquid separation mode:

[0028] 1. High-speed centrifugation, at 20°C, 12000rpm for 10min;

[0029] 2. Hollow fiber membrane filtration, flow rate 100ml min -1 , pressure 0.8Kg / cm 2 ;

[0030] 3. Roll membrane filtration, flow rate 100ml min -1 , pressure 10Kg / cm 2 ;

[0031] 4. Ceramic membrane filtration, flow rate 100ml min -1 , pressure 4Kg / cm 2 ;

[0032] Collect and obtain filtrate supernatant, gas chromatographic analysis, the result is listed in Table 1.

[0033] Table 1: Example 1 Filtration Clear Liquid Gas Chromatography Analysis Results

[0034]

[0035] Table 2: Example 2 Filtration Clear Liquid Gas Chromatography Analysis Results

[0036]

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Abstract

The invention relates to a method for purifying 2, 2-dimethyl-cyclopropane carboxamide produced by biocatalytic method. The method comprises: (1) conversion solution containing the 2, 2-dimethyl-cyclopropane carboxamide removes impurities by centrifugation or a membrane filtration system, so as to obtain supernatant fluid; (2) activated carbon which is 1-10 per mill of the quality of the supernatant fluid is added, and the decolorization of the activated carbon is carried out at 40-80 DEG C; (3) the pH value of the supernatant fluid after the decolorization is regulated to 8.5-13.5, macroporous adsorption resin is used for absorption till the supernatant fluid is saturated, the impurities are removed by water washing, hydrophilic solvent water solution with the volume concentration of 30-95 percent is further used for elution, the reduced pressure recovery of solvent and the concentration are carried out on eluent, so as to obtain a 2, 2-dimethyl-cyclopropane carboxamide crude product; (4) the 2, 2-dimethyl-cyclopropane carboxamide crude product is dissolved in hot water at 45-80 DEG C, stirred and crystallized at 0-4 DEG C, filtered and separated, and the 2, 2-dimethyl-cyclopropane carboxamide is finally obtained by drying crystals. The invention has the beneficial effects that the production process is simple and easy to operate, the product recovery rate is high and the industrial production is easy to realize.

Description

(1) Technical field [0001] The invention belongs to the field of biochemical industry, and in particular relates to a purification method for producing 2,2-dimethylcyclopropane formamide by a biocatalysis method. (2) Background technology [0002] (S)-(+)-2,2-Dimethylcyclopropanecarboxamide, CAS 75885-58-4, English name (S)-2,2-dimethyl-cyclopropane carboxamide, is the key to the synthesis of cilastatin Chiral intermediates. Cilastatin is a highly effective inhibitor of renal dehydrodipeptidase I. Its combination with imipenem——Taineng is currently the drug of choice for the treatment of severe infections, and the market demand is broad. [0003] Existing literature has reported (S)-(+)-2, the chemical synthesis method of 2-dimethylcyclopropanecarboxamide, as CH682485, JP6025956, EP0461541, EP0474200, WO2002 / 022543 etc., but these chemical resolution processes all There are serious environmental pollution, expensive chiral resolution reagents, harsh reaction conditions, le...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/58C07C231/24C12P13/02C12R1/01
Inventor 郑裕国郑仁朝徐建妙王远山沈寅初
Owner ZHEJIANG UNIV OF TECH
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