79778-02-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(Methylhydroxyphosphinyl)-2-oxobutyric acid serves as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic benefits, particularly in the treatment of various diseases and medical conditions.
Used in Chemical Research:
In the field of chemical research, 4-(Methylhydroxyphosphinyl)-2-oxobutyric acid is utilized as a valuable compound for studying the properties and reactions of butyric acid derivatives. Its hydroxymethylphosphinyl moiety provides a platform for exploring novel chemical reactions and mechanisms, contributing to the advancement of organic chemistry.
Used in Agrochemical Industry:
4-(Methylhydroxyphosphinyl)-2-oxobutyric acid finds application in the agrochemical industry as a precursor for the development of new pesticides and herbicides. Its unique structure can be modified to create compounds with enhanced efficacy and selectivity, leading to more effective and environmentally friendly agricultural solutions.
Used in Material Science:
In material science, 4-(Methylhydroxyphosphinyl)-2-oxobutyric acid can be employed as a building block for the synthesis of novel materials with specific properties. Its incorporation into polymers or other materials can lead to the development of new materials with improved characteristics, such as enhanced stability, reactivity, or selectivity.

Upstream product

• 15090-27-4 ethyl 3-(ethoxymethylphosphinyl)propionate 
• 95-92-1 oxalic acid diethyl ester 
• 166046-86-2 methyl(2-oxamoylethyl)phosphinic acid 
• 79778-35-1 methyl(2-ethoxycarbonyl)phosphinic acid 
• 76734-37-7 4-(ethoxy-(methyl)phosphinyl)-2-acetoxybutyronitrile 
• 80902-10-9 2-hydroxy-4-(hydroxy(methyl)phosphinyl)butanoic acid 
• 676-83-5 methyldichlorophosphane 
• 134745-23-6 ethyl 2-oxobut-3-enoate 
• 108736-44-3 Methyl-3-oxo-pentenoat 
• 221319-78-4 1-4-((ethoxy)(methyl)phosphoryl)butene 
• 73870-64-1 2-4-((ethoxy)(methyl)phosphoryl)butanone 
• 56-86-0 L-glutamic acid 
• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 

Downstream Products

• 131131-77-6 2,2-Bis-acetylamino-4-(hydroxy-methyl-phosphinoyl)-butyric acid 
• 79778-31-7 (E)-2-acetamido-4-(hydroxymethylphosphinyl)but-2-enoic acid 
• 131131-78-7 2-Acetamido-4-(hydroxymethylphosphinyl)-2-butenoic acid 
• 73777-49-8 L-homoalanine-4-yl(methyl)phosphinic acid hydrochloride 
• 77182-82-2 ammonium glufosinate 
• 82785-28-2 4-[hydroxy(methyl)phosphonyl]-DL-homoalanine 
• 35597-44-5 L-phosphinothricin 
• 328-50-7 α-ketoglutaric acid 
• 53369-07-6 L-phosphinothricin 
• 73679-07-9 (S)-(+)-phosphinothricin 
• 1352559-53-5 (Z)-2-methoxycarbonylamino-4-(hydroxy(methyl)phosphinyl)-2-butenoic acid 
• 131131-79-8 methyl (Z)-2-acetamido-4-(methoxymethylphosphinyl)but-2-enoate 
• 131131-81-2 methyl D-2-acetamido-4-(methoxymethylphosphinyl)butanoate 
• 131131-81-2 methyl L-2-acetamido-4-(methoxymethylphosphinyl)butanoate 

Relevant academic research and scientific papers

Development of a biocatalytic cascade for synthesis of 2-oxo-4-(hydroxymethylphosphinyl) butyric acid in one pot

2-Oxo-4-(hydroxymethylphosphinyl) butyric acid (PPO) is an important precursor compound for the broad-spectrum herbicide l-glufosinate (L-PPT). In this study, the gene of d-amino acid oxidase (DAAO) was cloned and expressed in Escherichia coli. By coupling exogenous catalase (CAT), a biocatalytic cascade was constructed for synthesis of PPO in one pot. The bioprocess was optimized on a 300 mL scale reaction by one factor at a time optimization. The conversion of this biocatalytic cascade achieved 46.8% towards 400 mM DL-PPT within 4 h. These results indicated that DAAO could be applied to the large-scale bioproduction of PPO and provide a promising route for the asymmetric synthesis of L-PPT by bio-enzymatic methods using PPO as the substrate.

METHODS FOR IMPROVING YIELDS OF L-GLUFOSINATE

Compositions and methods for the production of L-glufosinate are provided. The method involves converting racemic glufosinate to the L-glufosinate enantiomer or converting PRO to L-glufosinate in an efficient manner. In particular, the method involves the specific amination of PRO to L-glufosinate, using L-glutamate, racemic glutamate, or another amine source as an amine donor. PRO can be obtained by the oxidative deamination of D-glufosinate to PRO (2- oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid) or generated via chemical synthesis. PRO is then converted to L-glufosinate using a transaminase in the presence of an amine donor. When the amine donor donates an amine to PRO, L-glufosinate and a reaction by product are formed. Because the PRO remaining represents a yield loss of L-glufosinate, it is desirable to minimize the amount of PRO remaining in the reaction mixture. Degradation, other chemical modification, extraction, sequestration, binding, or other methods to reduce the effective concentration of the by-product, i.e., the corresponding alpha ketoacid or ketone to the chosen amine donor will shift the reaction equilibrium toward L-glufosinate, thereby reducing the amount of PRO and increasing the yield of L-glufosinate. Therefore, the methods described herein involve the conversion or elimination of the alpha ketoacid or ketone by-product to another product to shift the equilibrium towards L-glufosinate.

Novel method for synthesizing L-phosphinothricin key intermediate

The invention provides a novel method for synthesizing an L-phosphinothricin key intermediate. The method comprises the following steps: mixing a compound of a structure of a formula II and a compoundof a structure of a formula III, and distilling to obtain a compound of a structure of a formula IV; mixing the compound of the structure of the formula IV with an organic acid, and distilling to obtain a compound of a structure of a formula V; mixing the compound of the structure of the formula V, hydantoin and weak base, adding a first acid solution to regulate the pH value after the reaction,and filtering, washing and drying to obtain a compound of a structure of a formula VI; adding a strong alkaline solution into the compound of the structure of the formula VI, and reacting to obtain acompound of a structure of a formula VII; adding a second acid solution into the compound of the structure of the formula VII to regulate the pH value, distilling off water to obtain a solid, dissolving the solid with a third solvent, filtering, cooling, adding a fourth solvent, filtering again, washing and drying, thereby obtaining the compound of the structure of the formula I, namely the L-phosphinothricin key intermediate 4-(hydroxymethyl phosphonyl)-2-carbonyl butyric acid. The novel method disclosed by the invention is low in cost and high in yield.

Efficient purification process of 4-(methylhydroxyphosphoryl)-2-carbonylbutyric acid

The invention provides an efficient purification process of 4-(methylhydroxyphosphoryl)-2-carbonylbutyric acid. The efficient purification process comprises the following steps: adding a 4-(methylhydroxyphosphoryl)-2-carbonylbutyric acid crude product into a dehydrating agent, and mixing for dissolving, so as to obtain a first reaction system; cooling the first reaction system, so as to separate acyclization product; filtering the cyclization product so as to obtain a first filter cake, washing the first filter cake by virtue of a first solvent, drying, adding a second solvent, mixing, addingwater, and cooling, stirring, so as to obtain a second reaction system; continuing to cool the second reaction system, stirring for crystallization, filtering to obtain a second filter cake, washingthe second filter cake by virtue of a second solvent, and drying, so as to obtain a 4-(methylhydroxyphosphoryl)-2-carbonylbutyric acid pure product. The purification process provided by the inventionhas the advantages of high purification efficiency, simple method and mild conditions.

Glufosinate ammonium salt intermediate and synthesis method of glufosinate ammonium salt

The invention provides a glufosinate ammonium salt intermediate and a synthesis method of glufosinate ammonium salt. The glufosinate ammonium salt intermediate is a compound III (wherein a formula IIIis shown in the description); the synthesis method comprises the following steps: step (1): enabling a compound I (wherein a formula I is shown in the description) and oxygen gas to react and synthesize a compound II (wherein a compound II is shown in the description) in a Pd (II) catalysis system under the reaction conditions that the temperature is 20 to 60 DEG C and the pressure is 0.4 to 0.7MPa; step (2): dissolving the compound II (wherein the compound II is shown in the description) into an alkaline water solution and reacting with an oxidant at 0 to 50 DEG C; then carrying out acidification to synthesize the compound III (wherein the formula III is shown in the description), wherein R is selected from one of C1 to C5 alkyl; then dissolving the compound III (wherein the formula IIIis shown in the description) into a solvent and adding a catalyst to react with ammonia gas and hydrogen gas in sequence, so as to prepare the glufosinate ammonium salt, i.e., a compound IV (wherein aformula IV is shown in the description). Compared with a traditional glufosinate ammonium synthesis technology, the method provided by the invention has the advantages of no utilization of highly toxic cyanide and Grignard reaction, relatively moderate reaction conditions, easiness for controlling, short steps, high yield and low cost and is suitable for industrial production.

Synthesizing method for glufosinate-ammonium ammonium salt

The invention relates to a synthesizing method for glufosinate-ammonium ammonium salt. The synthesizing method comprises the following steps: 1) synthesizing methyl methoxyphosphoryl propionate by the reaction of methyl phosphite dimethyl phosphate with methyl acrylate and methyl alcohol; 2) synthesizing 2-[(methyl methoxy)phosphoryl]methyl-3-oxo-butyrate dimethyl ester by the Claisen condensation of methyl methoxyphosphoryl propionate and dimethyl oxalate; 3) under the acidic condition, carrying out the hydrolysis reaction to the 2-[(methyl methoxy)phosphoryl]methyl-3-oxo-butyrate dimethyl ester so as to generate 4-hydroxymethylphosphonic oxide butyric acid; and 4) under the catalyst function, successively reacting with ammonia gas and hydrogen by the 4-hydroxymethylphosphonic oxide butyric acid, and preparing the glufosinate-ammonium ammonium salt. The synthesizing method is capable of avoiding using cyanide poisonous materials. The format reaction is not used, the amount of the solvent used in the production process is small, the reaction condition is moderate and easily controlled, the synthesizing method is suitable for industrial production, the production is safe and convenient to operate, the reaction process is short, and the yield is high.

Synthetic method of phosphinothricin

The invention discloses a synthetic method of phosphinothricin. According to the method, methyl phosphorus dichloride compound and 2-carbonyl-3-butenoic acid ester compound are subjected to addition reaction, so that carbonyl butyric acid derivative is obtained, and the carbonyl butyric acid derivative is subjected to ammoniation and reduction, so that a phosphinothricin compound can be obtained. The method can not only avoid using virulent cyanide, obviously shortens the reaction route, reduces the technical steps for synthesizing phosphinothricin, is convenient to operate, and does not need recrystallization to remove ammonium salt, but also is high in yield, low in cost, high in the purity of the prepared phosphinothricin, and particularly applicable to industrial production.

Grass ammonium phosphine method for the preparation of (by machine translation)

The invention relates to a preparation method of glufosinate. The preparation method comprises the following steps: with a compound represented by a formula (I) as a starting material, reacting the compound represented by the formula (I) with cyanide RCN to obtain ketone nitrile; then hydrolyzing ketone nitrile in the presence of an acidic substance and water so as to obtain ketoacid; and reacting ketoacid successively with ammonia gas and hydrogen under the action of a catalyst so as to obtain glufosinate; wherein the compound represented by the formula (I) is cyclic phosphonic acid anhydride. The preparation method in the invention has the advantages of simple process, convenient operation, high product purity, high yield, no need for repeated recrystallization, ect.; and the final product of the preparation method is directly glufosinate ammonium, the step of converting glufosinate chloride into glufosinate ammonium is omitted, so the method has great economic benefit and is suitable for industrialization production.

Preparation method of 4-[hydroxy(methyl)phosphoryl]-2-oxobutanoic acid as glufosinate intermediate

The invention discloses a preparation method of 4-[hydroxy(methyl)phosphoryl]-2-oxobutanoic acid as a glufosinate intermediate. The method comprises the following steps: 1) proper organic solvent, alkaline substance and phase-transfer catalyst are added to cyclic phosphoric anhydride at the temperature of subzero 30 DEG C, stirred, heated to 25-50 DEG C, subjected to a reaction with diethyl oxalate at the room temperature and stirred, and a product is obtained through direct precipitation and filtration from the solvent; 2) water is added to the product, hydrogen chloride is introduced slowly, the pH is controlled, heating is performed, water is removed through rotary evaporation after the reaction is performed for 16 h, and a final product is obtained through vacuum drying. The method has the advantages that the problems of poor solubility and high probability of precipitation of cyclic phosphoric anhydride at a low temperature as well as high probability of ring opening of anhydride and high probability of decomposition of phosphate groups of cyclic phosphoric anhydride under an alkaline condition due to temperature increasing are solved, and the feasibility for preparing 4-[hydroxy(methyl)phosphoryl]-2-oxobutanoic acid as the glufosinate intermediate from cyclic phosphoric anhydride is realized successfully.

Synthetic method for L-type glufosinate ammonium

The invention relates to a synthetic method for L-type glufosinate ammonium. The synthetic method includes the steps that 4-(oxethyl-(methyl) phosphinyl)-2-acetoxyl butyl cyanide and hydrochloric acid react to obtain 4-(hydroxyl-(methyl) phosphinyl)-2-hydroxybutyric acid; 4-(hydroxyl-(methyl) phosphinyl)-2-hydroxybutyric acid reacts with a sodium hydroxide water solution to obtain 4-(sodium hydroxyl-(methyl) phosphinyl)-2-sodium hydroxyl butyrate; 4-(sodium hydroxyl-(methyl) phosphinyl)-2-sodium hydroxyl butyrate reacts with a sodium hypochlorite water solution to obtain 4-(sodium hydroxyl-(methyl) phosphinyl)-2-sodium carbonyl butyrate; 4-(sodium hydroxyl-(methyl) phosphinyl)-2-sodium carbonyl butyrate reacts with hydrogen chloride gas to obtain 4-(hydroxyl-(methyl) phosphinyl)-2-carbonyl butyric acid; 4-(hydroxyl-(methyl) phosphinyl)-2-carbonyl butyric acid reacts with liquid ammonia, and then hydrogen is introduced for reacting to obtain L-type glufosinate ammonium. The synthetic method is simple in technical process, small in pollution, high in yield and low in cost, the obtained finished product is levorotatory glufosinate ammonium with the efficient weeding effect, and the weeding effect of glufosinate ammonium is greatly improved.