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Synthesis method of chiral norvaline

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

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 The 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) by Andrey et al. n-valeric acid to obtain the method of D-norvaline, but the cost of this method is higher, the synthesis process is complicated, and its application limitation is arranged

Method used

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  • Synthesis method of chiral norvaline
  • Synthesis method of chiral norvaline
  • Synthesis method of chiral norvaline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The synthetic method of L-norvaline, take n-butyraldehyde and sodium cyanide, ammonium chloride as main starting raw material, make through following steps successively:

[0023] (1) Preparation of aminovaleronitrile:

[0024] In the mixed solvent that 50ml methanol and 200ml water are made into, add n-butyraldehyde (14.4g, 0.2mol), sodium cyanide (10.8g, 0.22mol), ammonium chloride (11.8g, 0.22mol), stir to dissolve, At this time, the solution was not separated; the temperature was controlled at about 70°C for 6 hours. After stopping the reaction, the reaction solution was extracted twice with 50 ml of ethyl acetate respectively, the organic phases were combined, and the crude product of aminovaleronitrile (12.6 g, 0.13 mol) was obtained after removing the solvent.

[0025] (2) cyano amidation, i.e. the preparation of racemic aminovaleramide:

[0026] The aminovaleronitrile crude product obtained in the previous step (9.8g, 0.1mol) was added dropwise to 32g of 98% co...

Embodiment 2

[0034] The synthetic method of L-norvaline, take n-butyraldehyde and sodium cyanide, ammonium chloride as main starting raw material, make through following steps successively:

[0035] (1) Preparation of aminovaleronitrile:

[0036]In the mixed solvent that 50ml ethanol and 200ml water are made into, add n-butyraldehyde (14.4g, 0.2mol), sodium cyanide (14.7g, 0.3mol), ammonium chloride (16.1g, 0.3mol), stir to dissolve, At this time, the solution was not separated; the reaction temperature was controlled at about 80°C for 8 hours. After stopping the reaction, the reaction solution was extracted twice with 50 ml of ethyl acetate respectively, the organic phases were combined, and the crude product of aminovaleronitrile (10.3 g, 0.11 mol) was obtained after removing the solvent.

[0037] (2) cyano amidation, i.e. the preparation of racemic aminovaleramide:

[0038] The aminovaleronitrile crude product obtained in the previous step (9.8g, 0.1mol) was added dropwise in 38g of 1...

Embodiment 3

[0046] The synthetic method of L-norvaline, take n-butyraldehyde and sodium cyanide, ammonium chloride as main starting raw material, make through following steps successively:

[0047] (1) Preparation of aminovaleronitrile:

[0048] In the mixed solvent that 66ml methanol and 200ml water are made into, add n-butyraldehyde (14.4g, 0.2mol), sodium cyanide (19.6g, 0.4mol), ammonium chloride (21.4g, 0.4mol), stir to dissolve, At this time, the solution was not separated; the reaction temperature was controlled at about 50° C. for 4 hours. After stopping the reaction, the reaction solution was extracted twice with 50 ml of ethyl acetate, the organic phases were combined, and the crude product of aminovaleronitrile (7.3 g, 0.07 mol) was obtained after removing the solvent.

[0049] (2) cyano amidation, i.e. the preparation of racemic aminovaleramide:

[0050] The aminovaleronitrile crude product obtained in the previous step (9.8g, 0.1mol) was added dropwise to 38g of 99% concent...

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Abstract

The invention discloses a synthesizing method of chiral norvaline, which comprises the following steps: adopting n-butyladehyde, sodium cyanide and ammonia chloride as raw material; proceeding cyano amidation; detaching; recrystallizing; hydrolyzing.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing chiral norvaline. Background technique [0002] [0003] The chiral norvaline with the molecular formula shown in S-1 is a key intermediate for the synthesis of the drug perindopril (the molecular formula shown in S-2). The existing synthesis methods of chiral norvaline are seldom reported. The patent JP7553587 adopts the fermentation method to produce it, and the yield is about 3.7g / L, which is far lower than the yield of amino acids produced by general fermentation, and it is difficult to meet the needs of industrial production. Chinese patent application 200410084417.7 discloses the technology of synthesizing L-norvaline with n-butyraldehyde and acetone cyanohydrin as raw materials, but the raw material acetone cyanohydrin is not easy to get, and the price is high; and the present invention adopts sodium cyanide as the reaction raw mat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/02C07C227/34C07C229/08
Inventor 陈新志钱超
Owner ZHEJIANG UNIV
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