Method for preparing phenylalanine compound

• US 10,640,465 B2
• Filed: 09/27/2017
• Issued: 05/05/2020
• Est. Priority Date: 09/27/2016
• Status: Active Grant

• Current Assignee: Shenzhen Chipscreen Biosciences Co., Ltd.
• Original Assignee: Shenzhen Chipscreen Biosciences Co., Ltd.
• Inventors: Lu, Xianping, Li, Zhibin, Wang, Xianghui
• Primary Examiner(s): Vajda, Kristin A
• Application Number:
  US16/337,207
• Publication Number:
  US 20190225582A1
• Time in Patent Office: 951 Days
• Field of Search: 548444
• CPC Class Codes: C07C 229/36 with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
• CPC Class Codes: C07D 209/86 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system

Abstract

Disclosed is a method for preparing 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propanoic acid. In the method 9-carbazole ethanol mesylate and methyl 2-[2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propionate are used as starting materials, and subjected to condensation, hydrolysis and acidification to obtain the target compound. The preparation method of the present invention is suitable for industrial production, and the target compound has a high purity.

Claims

1. A method for preparing 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl) ethoxy)phenyl)propanoic acid, comprising the following steps:

(a) reacting compound (I) with compound (II), to give compound (III);

2. The method according to claim 1, wherein step (a) is carried out in the presence of cesium carbonate.

3. The method according to claim 1, wherein step (a) is carried out at a temperature between 80 and 120°

C.

4. The method according to claim 1, wherein step (a) is carried out by using toluene as a solvent.

5. The method according to claim 1, wherein the hydrolysis of step (b) is conducted in the presence of a base.

6. The method according to claim 1, wherein the hydrolysis of step (b) is conducted in the presence of lithium hydroxide.

7. The method according to claim 1, wherein the step (b) is carried out by using N, N-dimethylformamide and water or tetrahydrofuran and water as a solvent.

8. The method according to claim 1, wherein step (c) is carried out in the presence of an inorganic acid.

9. The method according to claim 1, wherein step (c) is carried out in the presence of hydrochloric acid.

10. The method according to claim 1, wherein step (c) is carried out by using ethyl acetate and water as a solvent.