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Method for synthesizing D-norvaline using n-pentanoic acid

A technology of norvaline and nvaleric acid, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of high cost, complicated starting materials, complex synthesis process, etc., and achieve low cost, The effect of short production cycle and simple production process

Inactive Publication Date: 2007-08-01
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example, the article "D-Amino acid production by E.coli co-expressed three genes encoding hydantoin racemase, D-hydantoinase and N-carbamoyl-D-amino acid amidohydrolase." "Journal of Molecular Catalysis B: Enzymatic" 2005 , 32(5-6): 213-218; Article by Badorrey Ramon et al. "Stereodivergent addition of allylmetal reagents to imines derived from (R)-2,3-di-O-benzylglyceraldehyde by appropriate selection of metal and double stereodifferentiation. "" European Journal of Organic Chemistry " 2002, (22): 3763-3767 etc., but in the synthetic method of these bibliographical reports, starting material is complicated, perhaps needs to use complicated catalyst
Article by Alexandre Francois-Rene et al. "Amine-boranes: effective reducing agents for the deracemisation of DL-amino acid using L-amino acid oxidase from Proteus myxofaciens." "Tetrahedron Letters" 2002, 43(4): 707-710 and Galkin Andrey et al.'s article "Synthesis of optically active amino acids from α-keto acids with Escherichia coli cells expressing heterologous genes." "Applied and Environmental Microbiology" 1997, 63 (12): 4651-4656) disclosed that by splitting α- amino n-valeric acid to obtain the method of D-norvaline, but the cost of this method is higher, and the synthesis process is complicated, and its application limitation is arranged

Method used

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  • Method for synthesizing D-norvaline using n-pentanoic acid
  • Method for synthesizing D-norvaline using n-pentanoic acid
  • Method for synthesizing D-norvaline using n-pentanoic acid

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Effect test

Embodiment 1

[0022] The synthetic method of D-norvaline, take n-valeric acid as main starting raw material, make through following steps successively:

[0023] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0024] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (123.9g, 1.04mol) successively, oil Bath heating, reflux at 78 ° C for 4 hours, until no hydrogen chloride gas is released.

[0025] (2) bromination, preparation of α-bromovaleryl chloride:

[0026] Keep the liquid obtained in the previous step slightly boiling, and the reaction temperature is 80°C. Liquid bromine (60.5 g, 0.38 mol) dried with an equal volume of concentrated sulfuric acid is added dropwise to the flask, and the dropping process is completed within 6 hours. After the dropwise addition was completed, heating and stirring were stopped, and the mixture was allowed to stand ...

Embodiment 2

[0037] The synthetic method of D-norvaline, take n-valeric acid as main starting raw material, make through following steps successively:

[0038] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0039] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (85.8g, 0.72mol) successively, oil Bath heating, 60 ℃ reaction 8h, until no hydrogen chloride gas is released.

[0040] (2) bromination, preparation of α-bromovaleryl chloride:

[0041]Keeping the temperature of the liquid obtained in the previous step at 50°C, liquid bromine (115.2 g, o.72 mol) dried with an equal volume of concentrated sulfuric acid was added dropwise to the flask, and the dropping process was completed within 8 hours. After the dropwise addition was completed, heating and stirring were stopped, and the mixture was allowed to stand overnight. The next day, rectificat...

Embodiment 3

[0052] The synthetic method of D-norvaline, take n-valeric acid as main starting raw material, make through following steps successively:

[0053] (1) Acyl chloride, i.e. the preparation of n-pentanoyl chloride:

[0054] In the flask equipped with stirring, reflux condenser, dropping funnel, calcium chloride drying tube and thermometer, add n-valeric acid (36.7g, 0.36mol) and thionyl chloride (214.4g, 1.80mol) successively, water bath Reaction at 70°C for 6h.

[0055] (2) bromination, preparation of α-bromovaleryl chloride:

[0056] Keeping the temperature of the liquid obtained in the previous step at 70°C, liquid bromine (86.4 g, 0.54 mol) dried with an equal volume of concentrated sulfuric acid was added dropwise to the flask, and the dropping process was completed within 10 h. After the dropwise addition was completed, the stirring was stopped and left to stand overnight. The next day, rectification under reduced pressure collected 56 g of 88-90°C / 9mmHg fraction, which ...

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Abstract

The invention discloses a synthesizing method of D-norvaline, which comprises the following steps: adopting n-pentatonic acid as main original material; acylating and chlorinating; bromining; ammonifying; detaching; recrystallizing; hydrolyzing.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a synthesis method using n-valeric acid D-norvaline. Background technique [0002] [0003] The D-norvaline with the molecular formula shown in S-1 can be used as a D- source to synthesize some macrolides with D-, such as Pamamycin-607 and alkaloid (R)-Epilachnene . Since D-norvaline is not a natural amino acid, the existing literature reports are mainly based on chemical synthesis. For example, the article "D-Amino acid production by E.coli co-expressed three genes encoding hydantoin racemase, D-hydantoinase and N-carbamoyl-D-amino acid amidohydrolase." "Journal of Molecular Catalysis B: Enzymatic" 2005 , 32(5-6): 213-218; Article by Badorrey Ramon et al. "Stereodivergent addition of allylmetal reagents to imines derived from (R)-2,3-di-O-benzylglyceraldehyde by appropriate selection of metal and double stereodifferentiation. "European Journal of Organic Chemistry...

Claims

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Application Information

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IPC IPC(8): C07C227/06C07C227/34C07C229/08
Inventor 陈新志钱超
Owner ZHEJIANG UNIV
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