Preparation method for glufosinate
AssigneeLier Chemical Co., Ltd.
InventorsYongjiang Liu, Lei Zhou, Wei Zeng, Min Xu, Ke Cheng
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Abstract
A preparation method for glufosinate or a salt, an enantiomer or a mixture of enantiomers in all ratios thereof, the method being especially suitable for the preparation of glufosinate, and greatly shortening steps in an existing preparation process. Especially in the preparation of L-glufosinate, the product can effectively retain the ee value of the raw materials.
Claims30
A method for preparing a glufosinate compound of formula (I), a salt thereof, an enantiomer thereof, or a mixture of enantiomers thereof, which enantiomers may be present in any ratio,
- wherein the method comprises the following steps:
- a) reacting a compound of formula (II) or a salt thereof, an enantiomer thereof or a mixture of enantiomers thereof, which enantiomers may be present in any ratio,
- with one or more compounds of formula (III) or a mixture;
- wherein said mixture comprises one or more compounds of formula (IV) and one or more compounds of formula (V);
- or one or more compounds of formula (IV) and one or more compounds of formula (III);
- or one or more compounds of formula (V) and one or more compounds of formula (III);
- or one or more compounds of formula (III), one or more compounds of formula (IV), and one or more compounds of formula (V),
- wherein the reaction of a) results in a “reaction intermediate”;
- b) reacting the reaction intermediate which results from step a), wherein said reaction intermediate may or may not be in isolated form, with an acid or a base to obtain a glufosinate compound of formula (I) or a salt thereof, an enantiomer thereof, or a mixture of enantiomers thereof, which enantiomers may be present in any ratio;
- wherein when PG is an amino protecting group, the method further optionally includes the removal of the amino protecting group;
- further wherein:
- LG is Hal1, —OTs or Hal1
- Hal1 and Hal2 are each independently halogen selected from fluorine, chlorine, bromine or iodine;
- PG is hydrogen or an amino protecting group selected from —C(═O)R, —C(═O)OR and —S(═O)2R;
- A is —NHR1, —NR1R1′, or —OR1;
- R, R1, R1′, R2, R3 and R4 are each independently selected from the group consisting of C1-C6 alkyl, C3-10 cycloalkyl, C6-10 aryl, C6-12 aralkyl, 5- to 14-membered heteroaryl and 3- to 10-membered heterocyclyl,
- with the further proviso that when the mixture comprises a mixture of one or more compounds of formula (IV) and one or more compounds of formula (III);
- or a mixture of one or more compounds of formula (III), one or more compounds of formula (IV) and one or more compounds of formula (V);
- then
- R2 is either R3 or R4;
- and
- the chiral carbon atom is labeled with *;
- and
- with the further proviso that at least one of the following conditions is met:
- 1) the compound of formula (II) is not
- 2) the compound of formula (III) is not
- 3) the compound of formula (IV) is not
- 4) the compound of formula (V) is not
A compound of formula (II) or a salt thereof,
- wherein the compound of formula (II) is selected from the group consisting of:
Dependencies are inferred from the claim text.