Method for synthesizing derivative of beta-amino acid and intermediate product thereof

A synthesis method and derivative technology, applied in the direction of organic chemistry, can solve the problems of high reaction conditions, unsuitable for large-scale production, high raw material prices, etc., and achieve the effects of low pollution, simple waste treatment methods, and cheap prices

Active Publication Date: 2008-05-28
ASYMCHEM LAB FUXIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, the above three types of synthetic methods are not suitable for large-scale production due to the high price of raw materials, high reaction conditions, or the use of highly toxic substances.

Method used

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  • Method for synthesizing derivative of beta-amino acid and intermediate product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of (E)-N-cyclopropyl-2-hexanamide

[0031]Add dichloromethane (10ml / g) and trans-2-hexenoic acid (1eq.) to the reaction kettle, add N'N-dicarbonyldiimidazole (1.1eq.) to the system, after the addition is complete, the system is refluxed for 4.5h; Cool down to 35°C and add cyclopropylamine (2.4eq.). Incubate at -15°C for 12h. The system was suction filtered and rinsed with dichloromethane. The organic phase was washed with brine, dried, filtered with suction, and the filtrate was spin-dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of ethyl acetate and cyclohexane to obtain a solid with a yield of 80%.

[0032] 1HNMR (300MHz, CDCl3), δ0.501 (cyclopropyl CH2, m), δ0.772 (CH3, m), δ0.916 (CH2, m), δ1.460 (CH2, m), δ2.132 ( Cyclopropyl CH, m), δ6.160 (vinyl H, m), δ6.819 (vinyl H, m), δ7.294 (NH, m).

[0033] (2) Preparation of 3-propyloxirane-2-hexanoic acid cyclopropylamide

[0034] Add propionitrile (5L / mol...

Embodiment 2

[0046] (1) Preparation of (E)-N-n-octyl-2-butanamide

[0047] Add dichloroethane (20ml / g) and trans-2-butenoic acid (1eq.) to the reaction kettle, add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide salt to the system acid salt (2eq.), after the addition was complete, the system was refluxed for 4.5h; the temperature was lowered to 10°C, and n-octylamine (5eq.) was added dropwise. Incubate at 20°C for 12h. The system was suction filtered and rinsed with dichloromethane. The organic phase was washed with brine, dried, filtered with suction, and the filtrate was spin-dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of ethyl acetate to obtain a solid with a yield of 54%.

[0048] 1HNMR (300MHz, CDCl3), δ0.912 (n-octyl CH3, m), δ1.279 (4×n-octyl CH2, m), δ1.268 (n-octyl CH2 linked to CH3, m), δ1 .543 (CH2 of β linked to N, m), δ1.667 (CH3, m), δ2.934 (CH2 of α linked to N, m), δ6.198 (vinyl H, cis, m ), δ6.615 (vinyl H, m), δ7.548 (NH, ...

Embodiment 3

[0062] (1) Preparation of (E)-N-tert-butyl-2-hexanamide

[0063] Add dichloromethane (40ml / g) and trans-2-hexenoic acid (1eq.) to the reaction kettle, add thionyl chloride (1.1eq.) to the system, after the addition is complete, the system is refluxed for 4.5h; tert-butyl amine (3.5 eq.). Incubate at 16°C for 12h. The system was suction filtered and rinsed with dichloromethane. The organic phase was washed with brine, dried, filtered with suction, and the filtrate was spin-dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of ethyl acetate and cyclohexane to obtain a solid with a yield of 58%.

[0064] 1HNMR (300MHz, CDCl3), δ0.871 (CH3, m), δ1.223 (tert-butyl CH3, s), δ1.296 (CH2, m), δ1.798 (CH2, m), δ6.103 ( Vinyl H, m), δ6.457 (vinyl H, m), δ7.357 (NH, m).

[0065] (2) Preparation of 3-propyloxirane-2-hexenoic acid tert-butylamide

[0066] Add acetonitrile (5L / mol) and water (1L / mol) to the reaction kettle at one time, start sti...

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Abstract

The invention provides a synthesis method of beta-amino acid derivative, and relative intermediate product, in particular to a synthesis method of formula (I) and relative intermediate product. The invention is characterized in that the invention uses commercialized material as formula (II) (trans-, E-type) as initial material, to obtain final product which formula is (III) via chemical reaction with mild condition. The invention has easily accessible starting material, stable technological condition and support for scaled industrial production.

Description

(1) Technical field: [0001] The present invention relates to a synthetic method of derivatives of β-amino acids and intermediate products thereof, especially synthetic methods and their intermediates. (two) background technology: [0002] Derivatives of β-amino acids can be introduced into peptide drugs to modify the structure of peptide chains and enhance their stability and activity in vivo; in addition, they can also be used as anti-tumor drugs, using amino acid derivatives as enzyme inhibitors to Treat tumors, or transform cancer cells into amino acid derivatives, so as to achieve the purpose of treating tumors. [0003] At this stage, the methods for preparing such compounds mainly include the following three categories: [0004] 1. Using α-amino acid as raw material, it can be obtained by acylation, reduction to aldehyde, addition of NaCN, and hydrolysis. (1.V.P.Kukhar, H.R.Hudson, Eds., Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/04C07C233/02C07C245/14C07D303/48
Inventor 洪浩詹姆斯·盖吉陈朝勇韦建黄志杨玉龙
Owner ASYMCHEM LAB FUXIN
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