Method of producing L-glufosinate

Patent metadata

Field	Value
Publication number	US-12534482-B2
Application number	US-201917415096-A
Country	US
Kind code	B2
Filing date	Nov 29, 2019
Priority date	Jan 11, 2019
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

Provided is a method for preparing L-glufosinate from an L-homoserine derivative compound, the method including a step (step a) of preparing a compound of Chemical Formula 2 from a compound of Chemical Formula 1, and a step (step b) of preparing a compound of Chemical Formula 3 from the compound of Chemical Formula 2.

First claim

The invention claimed is:

1 . A method for preparing L-glufosinate from an L-homoserine compound of the following Chemical Formula 1, the method comprising a step a of preparing a compound of the following Chemical Formula 2 from the compound of the following Chemical Formula 1, and a step b of preparing a compound of the following Chemical Formula 3 from the compound of Chemical Formula 2,
wherein the step a comprises a step a-1 of preparing the compound of Chemical Formula 2 by reacting the compound of Chemical Formula 1 with a halogenating agent, at least one R 2 —OH, and a compound of the following Chemical Formula 5,

where in the above formulas,
R 1 is R a —(C═O)—, where R a is hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms,
R 2 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms, or —Si(R b )(R c )(R d ), where R b , R c and R d independently of one another are a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms,
R 3 and R 4 independently of one another are hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted alkynyl group having 1 to 6 carbon atoms,
R 5 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 6 carbon atoms, and
substituents of the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, and heteroaryl group independently of one another are at least one selected from hydrogen, halogen, a carboxyl group (—COOH), an amino group (—NH 2 ), a nitro group (—NO 2 ), a cyano group (—CN), an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms.

2 . The method for preparing L-glufosinate according to claim 1 , wherein the R 1 is acetyl or succinyl.

3 . The method for preparing L-glufosinate according to claim 1 , wherein the R 2 is any one selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl, phenyl and naphthyl.

4 . The method for preparing L-glufosinate according to claim 1 , wherein the R 3 and R 4 independently of one another are selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl and hexyl.

5 . The method for preparing L-glufosinate according to claim 1 , wherein the compound of Chemical Formula 1 is prepared from a fermentation liquid containing the precursor of the compound of Chemical Formula 1.

6 . The method for preparing L-glufosinate according to claim 1 , wherein the halogenating agent includes at least one selected from the group consisting of HCl, HBr, HI, phosgene, SOCl 2 , oxalyl chloride, trimethylsilyl halide, sodium iodide (NaI), triethylsilane, (CH 2 CH 3 ) 3 SiH)+palladium chloride (PdCl 2 )+methyl iodide (CH 3 I), POCl 3 , PCl 3 , PCl 5 , PBr 3 , PI 3 , H 2 SO 4 +KBr, P+Cl 2 , P+Br 2 , P+I 2 , TiCl 4 , ZnCl 2 and BBr 3 .

7 . The method for preparing L-glufosinate according to claim 1 , wherein the R 2 —OH includes at least one selected from the group consisting of methanol, ethanol, n-propanol, iso-propanol, butanol, pentanol, hexanol, benzyl alcohol, phenol and naphthol.

8 . The method for preparing L-glufosinate according to claim 1 , wherein a content of the R 2 —OH is 1 to 60 equivalents based on 1 equivalent of the compound of Chemical Formula 1.

9 . The method for preparing L-glufosinate according to claim 1 , wherein a content of the halogenating agent is 0.1 to 10 equivalents based on 1 equivalent of the compound of Chemical Formula 1.

10 . The method for preparing L-glufosinate according to claim 1 , wherein the step c is carried out at a temperature of 20 to 100° C. for a reaction time of 0.1 to 30 hours.

11 . The method for preparing L-glufosinate according to claim 1 , wherein the compound of Chemical Formula 5 includes any one selected from the group consisting of diethylmethylphosphinate (DMP), ethylmethylphosphinate (EMP) and butylmethylphosphinate (BMP).

12 . The method for preparing L-glufosinate according to claim 1 , wherein the content of the compound of Chemical Formula 5 is 0.5 to 10 equivalents based on 1 equivalent of the compound of Chemical Formula 1.

13 . The method for preparing L-glufosinate according to claim 1 , wherein the step a-1 is carried out at a temperature of 80 to 180° C. for 0.1 to 20 hours.

14 . The method for preparing L-glufosinate according to claim 1 , wherein the step b is carried out by hydrolyzing the compound of Chemical Formula 2 under an acid catalyst.

15 . The method for preparing L-glufosinate according to claim 14 , wherein the acid catalyst includes at least one selected from the group consisting of acetic acid, HCl, H 2 SO 4 and KF—Al 2 O 3 .

16 . The method for preparing L-glufosinate according to claim 1 , wherein the step b is carried out at a temperature of 20 to 150° C. for 0.1 to 30 hours.

17 . The method for preparing L-glufosinate according to claim 1 , wherein the L-glufosinate includes at least one selected from hydrochloride of L-glufosinate, sulfate of L-glufosinate, carbonate of L-glufosinate, sodium salt of L-glufosinate, and ammonium salt of L-glufosinate.

Assignees

• Cj Cheiljedang Corp

Inventors

• Jeon Jinwoo
• Lee Joo Young
• Lee Changsuk
• Kim Hyunjin
• Moon Jun Ok
• Oh In Seok

Classifications

• C07C233/05

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C231/00

  Preparation of carboxylic acid amides · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07F9/3205

  the acid moiety containing a substituent or a structure which is considered as characteristic · CPC title

• C07F9/301 Primary

  Acyclic saturated acids which can have further substituents on alkyl · CPC title