Method of preparing L-homoserine

Patent metadata

Field	Value
Publication number	US-11840496-B2
Application number	US-202017610731-A
Country	US
Kind code	B2
Filing date	Sep 9, 2020
Priority date	Sep 10, 2019
Publication date	Dec 12, 2023
Grant date	Dec 12, 2023

Abstract

Provided is a method of preparing L-homoserine, the method including contacting an L-homoserine derivative with a solid acid catalyst.

First claim

The invention claimed is:

1. A method of preparing L-homoserine, the method comprising:
contacting an L-homoserine derivative represented by the following Formula 1 with a solid acid catalyst:

in Formula 1,
R 1 is R a —(C═O)—,
R a is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted alkynyl group having 2 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, and
substituents of the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the aryl group, and the heteroaryl group are each independently halogen, —COOH, —COCH 3 , —NH 2 , —NO 2 , a —CN, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms.

2. The method of claim 1 , wherein R 1 is acetyl or succinyl.

3. The method of claim 1 , wherein the contacting is contacting the L-homoserine derivative represented by Formula 1 with an aqueous solution comprising water and the solid acid catalyst.

4. The method of claim 1 , wherein the solid acid catalyst comprises a resin catalyst.

5. The method of claim 4 , wherein the solid acid catalyst comprises a cation exchange resin catalyst.

6. The method of claim 5 , wherein the cation exchange resin catalyst comprises one or more acidic functional groups selected from —SO 3 H and —COOH.

7. The method of claim 5 , wherein the cation exchange resin catalyst comprises a structure in which one or more acidic functional groups selected from —SO 3 H and —COOH are linked to a polystyrene-divinylbenzene copolymer.

8. The method of claim 4 , wherein the contacting is carried out in a resin tower comprising the solid acid catalyst.

9. The method of claim 1 , wherein a content of the solid acid catalyst is 0.1 equivalent to 10 equivalents with respect to 1 equivalent of the L-homoserine derivative represented by Formula 1.

10. The method of claim 3 , wherein the aqueous solution comprising water and the solid acid catalyst is at pH of 1 to 5.

11. The method of claim 1 , wherein the contacting is carried out at a temperature of 20° C. to 150° C.

12. The method of claim 1 , wherein the contacting is carried out for 0.1 hr to 20 hr.

13. The method of claim 1 , wherein the contacting comprises:
supplying the L-homoserine derivative represented by Formula 1;
producing L-homoserine by contacting the L-homoserine derivative represented by Formula 1 with the solid acid catalyst; and
discharging the L-homoserine.

14. The method of claim 13 , wherein the supplying the L-homoserine derivative represented by Formula 1 and the discharging L-homoserine are continuously carried out.

15. The method of claim 1 , the method further comprising:
collecting the L-homoserine.

Assignees

• Cj Cheiljedang Corp

Inventors

• Kang Min Kyu
• Lee Jung Min
• Kim Min Sup
• Kim Il Chul
• Lee In Sung
• Jung Jun Young

Classifications

• C07C227/32 Primary

  by stereospecific synthesis · CPC title

• B01J31/10

  sulfonated · CPC title

• B01J2231/005

  General concepts, e.g. reviews, relating to methods of using catalyst systems, the concept being defined by a common method or theory, e.g. microwave heating or multiple stereoselectivity · CPC title

• B01J2531/002

  Materials · CPC title

• C07C227/16 Primary

  by reactions not involving the amino or carboxyl groups · CPC title