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Process for production of optically active aminophosphinylbutanoic acid

一种氨基氧膦基丁酸、旋光性的技术，应用在旋光性氨基氧膦基丁酸类的制备领域，能够解决催化效率不高、铑催化剂昂贵、后处理和纯化步骤复杂等问题，达到高光学纯度、高效且光学纯度的效果

Active Publication Date: 2009-07-29
MITSUI CHEM AGRO INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, both methods have the following problems: it is necessary to perform the reaction at a low substrate concentration; the work-up and purification steps are complicated; more than an equimolar amount of an expensive optically active amino acid must be used in the transamination reaction, etc.
However, rhodium catalysts are very expensive and not very efficient

Method used

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  • Process for production of optically active aminophosphinylbutanoic acid
  • Process for production of optically active aminophosphinylbutanoic acid
  • Process for production of optically active aminophosphinylbutanoic acid

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preparation example Construction

[0034] In the preparation method of the present invention, the optically active aminophosphine oxide represented by the above general formula (2) is obtained by asymmetric hydrogenation of the compound represented by the general formula (1) in the presence of a ruthenium-optical phosphine complex butyric acid.

[0035]

[0036] (In general formula (1), R 1Represents an alkyl group with 1 to 4 carbon atoms, R 2 Represents a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, R 3 Represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryl group, an aryloxy group or a benzyloxy group, R 4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. )

[0037] For the compound represented by the general formula (1) used in the present invention and the optically active aminophosphinyl butyric acids represented by the general formula (2) prepared by the present invention, R 1 , R 2 , R 3 and R 4 group shown....

Embodiment 1

[0090] Preparation of (S)-2-Acetamido-4-Hydroxymethylphosphinylbutanoic Acid

[0091]

[0092] Add (Z)-2-acetamido-4-hydroxymethylphosphinyl-2-butenoic acid (4.0 g, 18 mmol) and (RuCl (p-cymene) (S) in a 200 ml autoclave -binap)Cl (8.4mg, 0.009mmol) and methanol (20ml), nitrogen substitution and hydrogen substitution were carried out. The temperature in the autoclave was set to 70° C., hydrogen gas was injected up to 1 MPa, and the reaction solution was stirred at the same temperature for 5 hours. Take a part of the reaction solution as a sample. After confirming the completion of the reaction by performing high performance liquid chromatography (HPLC) analysis on the sample, the reaction solution was cooled to room temperature, and after hydrogen gas was released, the reaction solution was transferred to a 100ml flask. After removal of methanol in vacuo and addition of water (20ml), the aqueous phase was washed twice with toluene (10ml) to give (S)-2-acetamido-4-hydroxym...

Embodiment 2～4

[0095] Preparation of (S)-2-Acetamido-4-Hydroxymethylphosphinylbutanoic Acid

[0096] Except that the amount of (RuCl (p-cymene) (S)-binap) Cl was doubled, and the reaction time and reaction temperature were changed as shown in Table 1, the same operation as in Example 1 was carried out. The results are shown in Table 1. Also, the conversion rates were all 100%.

[0097] (Table 1)

[0098] Example

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Abstract

A process for producing an optically active aminophosphinylbutanoic acid represented by the general formula (2), comprising the step for conducting the asymmetric hydrogenation of a compound represented by the general formula (1) in the presence of a ruthenium-(optically active phosphine) complex. In the general formula (2), R1 represents an alkyl group having 1 to 4 carbon atoms; R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R3 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryl group, an aryloxy group or a benzyloxy group; R4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and symbol '*' means that a carbon having this symbol is an asymmetric carbon atom. In the general formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms; R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R3 represents an alkyl group having 1 to 4 carbonatoms, an alkoxy group having 1 to 4 carbon atoms, an aryl group, an aryloxy group or a benzyloxy group; R4 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; The process enables to produce a compound useful as a herbicide such as L-AHPB, at good efficiency and at high asymmetric yield.

Description

technical field [0001] The present invention relates to an optically active aminophosphinylbutyrate important as an intermediate of a compound useful for herbicides such as L-2-amino-4-(hydroxymethylphosphinyl)butyric acid (hereinafter abbreviated as L-AHPB) Methods of preparation of acids. Background technique [0002] DL-2-amino-4-(hydroxymethylphosphinyl) butyric acid (hereinafter referred to as DL-AHPB) is a known compound with herbicidal activity, and is used as an effective broad-spectrum herbicide (patent-opened Zhao 52- Bulletin No. 139727). However, the herbicidal activity of DL-AHPB is about half of that of L-AHPB, and it has been clarified that the main substance with herbicidal activity is L-AHPB (JP-A-55-000025 and JP-A-59-219297). Therefore, there is a strong need to develop a method for selectively and efficiently producing L-AHPB. [0003] Conventionally, methods for producing L-AHPB include (a) a method using microorganisms and enzymes, and (b) an asymmet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30C07F9/32C07B53/00C07B61/00
CPCC07F9/301C07B53/00C07F9/3211B01J31/28C07F9/30C07F9/32C07B61/00
Inventor 箕轮宣人中西希三富正明奈良秀树横泽亨
Owner MITSUI CHEM AGRO INC
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