Method of producing l-glufosinate
Through the reaction of L-lactone derivative compounds with halogenating agents and phosphorus compounds, combined with acid-catalyzed hydrolysis, the problems of complex preparation and low yield of glufosinate ammonium L-isomer in the existing technology are solved, and high efficiency, Simple preparation of high optical purity L-glufosinate.
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preparation example Construction
[0029] The preparation method of L-glufosinate-ammonium according to one embodiment is the method for preparing L-glufosinate-ammonium by L-lactone derivative compound, comprising: the step of preparing the compound of following Chemical formula 2 by the compound of following Chemical formula 1 (step a); and a step of preparing L-glufosinate of the following chemical formula 3 from the compound of the above chemical formula 2 (step b).
[0030]
[0031]
[0032]
[0033]
[0034]
[0035]
[0036] In the above formula,
[0037] R 1 is R a -(C=O)-, where R a is hydrogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkenyl having 1 to 6 carbon atoms, substituted or unsubstituted having 1 to 6 carbon atoms Alkynyl, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, or substituted or unsubstituted aryl having 2 to 10 carbon atom hetero...
Embodiment 1
[0135] Embodiment 1: use N-acetyl-L-homoserine lactone to prepare L-glufosinate-ammonium (using the second intermediate compound (1))
[0136] (Step 1-1: Preparation of ethyl 2-(acetylamino)-4-chlorobutyrate)
[0137]
[0138] To a solution obtained by dissolving 4 g (28 mmol) of N-acetyl-L-homoserine lactone in 60 mL of ethanol at 0° C., thionyl chloride (6.6 g, 56 mmol) was slowly added to prepare a reaction solution. The prepared reaction solution was stirred at 80° C. for 3 hours. Then, 1 N NaOH (aq) was added to the reaction-completed solution for neutralization, followed by concentration under reduced pressure to prepare a concentrate. The prepared concentrate was diluted with ethyl acetate and washed once with brine. Anhydrous magnesium sulfate (MgSO 4 ) after drying, filtered, and the filtrate was concentrated under reduced pressure to obtain a residue containing ethyl 2-(acetylamino)-4-chlorobutyrate.
[0139] The resulting residue was separated by column chr...
reference example 1
[0149] Reference Example 1: Preparation of N-acetyl-L-homoserine lactone
[0150]
[0151] To an aqueous solution of O-acetyl-L-homoserine (II) (1 g, 6.2 mmol) dissolved in 30 mL of water, NaOH (40 wt.% aqueous solution) as a base catalyst was slowly added to prepare a pH 9 reaction solution. Then, the prepared reaction solution was stirred at 25° C. for 30 minutes. Then, after heating the reaction solution to 50 degreeC, it stirred at 50 degreeC for 5 hours. Then, 1N HCl(aq) was added to the reaction-completed solution for neutralization, followed by concentration under reduced pressure to prepare a concentrate. After the prepared concentrate was cooled to 0°C, ethanol was added thereto, the mixture was stirred, and filtered under reduced pressure to obtain 0.98 g (yield 98%) of N-acetyl-L-homoserine (III-1) as white solid.
[0152] 1 H NMR (400MHz, DMSO-d6): δ7.68(d, J=8Hz, 1H), 3.96(m, 1H), 3.40(t, J=6.8Hz, 2H), 1.83(s, 3H), 1.81 (m,1H),1.61(m,1H)
[0153]
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