Method for producing N-acetyl dipeptide and N-acetyl amino acid

Patent metadata

Field	Value
Publication number	US-12018047-B2
Application number	US-201917282855-A
Country	US
Kind code	B2
Filing date	Nov 12, 2019
Priority date	Nov 12, 2018
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

Provided is a method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method including producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride.

First claim

The invention claimed is:

1. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein the reaction is performed in the presence of a catalyst, wherein the catalyst is calcium chloride or calcium hydroxide.

2. The method of claim 1 , wherein the reaction is performed in an organic acid solvent.

3. The method of claim 2 , wherein the solvent is carboxylic acid.

4. The method of claim 2 , wherein the solvent is acetic acid.

5. The method of claim 1 , wherein the amino acid is alanine, cysteine, aspartic acid, glutamic acid, phenylalanine, glycine, histidine, isoleucine, lysine, leucine, methionine, asparagine, proline, glutamine, arginine, serine, threonine, valine, tryptophan, or tyrosine.

6. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein the reaction is performed in the presence of a catalyst, wherein a molar ratio of the catalyst to the amino acid is 0.01 to 0.4.

7. The method of claim 2 , wherein the solvent is 0.1 time to 5 times the mass of the amino acid.

8. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein the reaction is performed at 10° C. to 30° C.

9. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein the reaction is performed for 3 hours to 12 hours.

10. The method of claim 1 , further comprising, after producing the N-acetyl dipeptide and N-acetyl amino acid, obtaining a liquid concentrate by concentrating the reaction solution comprising the reaction product obtained in the above reaction or obtaining crystals by crystallizing the reaction solution comprising the reaction product or the liquid concentrate.

11. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein a molar ratio of the N-acetyl dipeptide to the N-acetyl amino acid is 0.5 or more.

12. A method of preparing an N-acetyl dipeptide and an N-acetyl amino acid, the method comprising producing the N-acetyl dipeptide and the N-acetyl amino acid by reaction of an amino acid with acetic anhydride or acetyl chloride, wherein a molar ratio of the N-acetyl dipeptide to the N-acetyl amino acid is 0.5 to 9.0.

Assignees

• Cj Cheiljedang Corp

Inventors

• Lee Joo Young
• Lee Chang Suk
• Jeon Jin Woo
• Moon Jun Ok
• Park Jin Seung

Classifications

• C07K1/02

  in solution {(C07K1/003, C07K1/006 take precedence)} · CPC title

• C07C319/26

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C319/12

  by reactions not involving the formation of mercapto groups · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• B01J23/02

  of the alkali- or alkaline earth metals or beryllium · CPC title