US 12,252,502 B2
L-glufosinate intermediate and L-glufosinate preparation method
Jinwoo Jeon, Seoul (KR); Joo Young Lee, Seoul (KR); Changsuk Lee, Seoul (KR); Hyunjin Kim, Seoul (KR); Jun Ok Moon, Seoul (KR); and In Seok Oh, Seoul (KR)
Assigned to CJ CHEILJEDANG CORPORATION, Seoul (KR)
Appl. No. 17/311,743
Filed by CJ CheilJedang Corporation, Seoul (KR)
PCT Filed Nov. 29, 2019, PCT No. PCT/KR2019/016788
§ 371(c)(1), (2) Date Jun. 8, 2021,
PCT Pub. No. WO2020/145513, PCT Pub. Date Jul. 16, 2020.
Claims priority of application No. 10-2019-0004164 (KR), filed on Jan. 11, 2019; application No. 10-2019-0005282 (KR), filed on Jan. 15, 2019; application No. 10-2019-0005283 (KR), filed on Jan. 15, 2019; application No. 10-2019-0005404 (KR), filed on Jan. 15, 2019; and application No. 10-2019-0005405 (KR), filed on Jan. 15, 2019.
Prior Publication US 2022/0024955 A1, Jan. 27, 2022
Int. Cl. C07F 9/54 (2006.01); C07C 231/12 (2006.01); C07D 307/33 (2006.01); C07F 7/18 (2006.01); C07F 9/30 (2006.01); C07F 9/32 (2006.01)
CPC C07F 9/5428 (2013.01) [C07C 231/12 (2013.01); C07D 307/33 (2013.01); C07F 7/1896 (2013.01); C07F 9/301 (2013.01); C07F 9/3205 (2013.01); C07B 2200/07 (2013.01)] 21 Claims
 
1. A method for preparing a compound of Chemical Formula 2, the method comprising a step a of preparing a compound of the following Chemical Formula 2 from a compound of the following Chemical Formula 1,
wherein the step a comprises
(i) a step b of preparing a compound of the following Chemical Formula 3 by reacting the compound of Chemical Formula 1 with a first base catalyst, or
(ii) a step b-1 of preparing a compound of the following Chemical Formula 4 by reacting the compound of Chemical Formula 1 with a second acid catalyst,

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
where in the above formulas,
R1 is Ra—(C═O)—, where Ra is 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,
R2 is 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(Rb)(Rc)(Ra), where Rb, Rc and Rd 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,
X is halogen, 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 halogen, a carboxyl group (—COOH), an amino group (—NH2), a nitro group (—NO2), 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.