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Microbiological process for the preparation of amides

A technology of microbiology and microbial strains, applied in the field of amide preparation, which can solve problems such as inability to apply chemically specific substrates

Active Publication Date: 2020-10-09
哥伦比亚有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, these methods are usually only applicable to specific species of nitriles and cannot be applied to substrates with chemical properties that may be very different from each other.

Method used

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  • Microbiological process for the preparation of amides
  • Microbiological process for the preparation of amides
  • Microbiological process for the preparation of amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 2-Chloroacetamide

[0064] NHase was ground in a mortar and added to potassium phosphate buffer (10 mM, pH=7.4) (9 mL) in a 50 mL Erlenmeyer flask. The suspension was mixed by vortexing, and 2-chloroacetonitrile (38 mg, 0.5 mmol) was added to the suspension dissolved in MeOH (1 mL). The reaction was stirred by rotary shaking at 25°C and 250 rpm. After the reaction 1 H-NMR. Samples (1 mL) were analyzed after 1.5, 2.5, 4 and 7 hours. The sample was mixed with MeOH (2 mL), filtered and evaporated under vacuum. After 1.5 hours, complete conversion to 2-chloroacetamide was observed.

[0065] 1 H-NMR (CD 3 OD, 300.13MHz): 4.05-4.83 (s, 2H), comparable to commercially available 2-chloroacetamide samples.

Embodiment 2

[0067] 2,2-diethoxyacetamide

[0068] NHase was ground in a mortar and added to potassium phosphate buffer (10 mM, pH=7.4) (9 mL) in a 50 mL Erlenmeyer flask. The suspension was mixed by vortexing, and 2,2-diethoxyacetonitrile (65 mg, 0.5 mmol) was added to the suspension dissolved in MeOH (1 mL). The reaction was stirred by rotary shaking at 25°C and 250 rpm. After the reaction 1 H-NMR. Samples (1 mL) were analyzed after 1.5, 2.5, 4 and 7 hours. The sample was mixed with MeOH (2 mL), filtered and evaporated under vacuum. After 1.5 hours, complete conversion to 2,2-diethoxyacetamide was observed.

[0069] 1 H-NMR (CD 3 OD, 300.13MHz): 1.44(t, 6H, 3 J HH =6.0Hz), 3.61-3.70 (m, 4H), 4.81 (s, 1H), comparable to commercially available 2,2-diethoxyacetamide samples.

Embodiment 3

[0071] tert-Butyl 4-carbamoylpiperidine-1-carboxylate

[0072] NHase was ground in a mortar and added to potassium phosphate buffer (10 mM, pH=7.4) (9 mL) in a 50 mL Erlenmeyer flask. The suspension was mixed by vortexing, and tert-butyl 4-cyanopiperidine-1-carboxylate (105 mg, 0.5 mmol) was added to the suspension dissolved in MeOH (1 mL). The reaction was stirred by rotary shaking at 25°C and 250 rpm. HPLC-MS was performed after the reaction. Samples (1 mL) were analyzed after 1.5, 2.5, 4 and 7 hours. Samples were mixed with MeOH (2 mL), filtered and injected directly into HPLC. After 7 hours, 40% conversion to tert-butyl 4-carbamoylpiperidine-1-carboxylate was observed.

[0073] MS (ES + ): m / z: 173.0 [M-55]. MS (ES - ): m / z: 227.0 [M-1].

[0074] The HPLC chromatogram is comparable to a synthetic sample of tert-butyl 4-carbamoylpiperidine-1-carboxylate. RRT 3 = 1, RRT 3a = 0.87.

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Abstract

A microbiological process for the preparation of amides from the corresponding nitriles by enzymatic hydrolysis with nitrile hydratase enzyme from a bacterial strain of Rhodococcus biphenylivorans species is described.

Description

technical field [0001] The present invention relates to a process for the preparation of amides, more particularly to a process for the preparation of amides from the corresponding nitriles by enzymatic hydrolysis with nitrile hydratase from a strain of the genus Rhodococcus biphenyllivorans. Amide method. Background technique [0002] Nitriles are important precursors for the synthesis of amides and carboxylic acids, and are widely used as pharmaceutical active ingredients or advanced intermediates in their synthesis. [0003] The chemical hydrolysis of nitriles from carboxylic acids via intermediate amides requires severe conditions such as strong acids or bases at high temperatures (100 °C) and long reaction times. Amides are initially formed, but the amides are hydrolyzed by acid or base treatment to rapidly form carboxylic acids. Given the conditions to be used, chemical hydrolysis is often not suitable for the preparation of active pharmaceutical ingredients or their...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/02C12R1/01C12N9/88
CPCC12Y402/01084C12N9/88C12P13/02C12R2001/01C12N1/205
Inventor S·托尼奥洛
Owner 哥伦比亚有限公司
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