US 2025/0154095 A1 · SYNTHESIS METHOD OF AVENANTHRAMIDE C

Abstract

The present disclosure relates to a synthesis method of Avenanthramides, and more particularly, to a new large-scale synthesis method capable of obtaining Avenanthramide C with high yield through a pathway of introducing a protecting group to starting materials, 2-Amino-5-hydroxy benzoic acid and Caffeic acid, synthesizing the compound introduced with the protecting group through a nucleophilic substitution (SN2) reaction in the presence of oxalyl chloride ((COCl)2) and N,N-dimethylformamide (DMF), and removing the protecting group.

Claims19

Dependent claims

A synthesis method of avenanthramide C comprising:

as illustrated in the following Reaction Formula A,
Step 1 of reacting Compound 1 in the presence of methyl alcohol and an acid catalyst to obtain Compound 2 having a methyl protecting group introduced to a carbonyl group;
Step 2 of reacting Compound 3 and acetic anhydride in the presence of a first organic solvent to obtain Compound 4 having an acetyl protecting group introduced to a hydroxyl group of benzene;
Step 3 of reacting Compound 2 and Compound 4 in the presence of a second organic solvent to obtain Compound 5;
Step 4 of removing the acetyl protecting group from the Compound 5 to obtain Compound 6;
and
Step 5 of removing the methyl protecting group from the Compound 6 to obtain Compound 7:

4 more elements

Dependencies are inferred from the claim text.

Facts

Application

18/730,530Filed 6 May 2022

Priority

KR 10-2022-000843020 Jan 2022

Published

15 May 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 231/02
Preparation of carboxylic acid amides: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
C07C 231/12
Preparation of carboxylic acid amides: by reactions not involving the formation of carboxamide groups
C07C 227/16
From compounds containing already amino and carboxyl groups or derivatives thereof: by reactions not involving the amino or carboxyl groups
C07C 227/18
From compounds containing already amino and carboxyl groups or derivatives thereof: by reactions involving amino or carboxyl groups, e.g.…

Synthesis method of avenanthramide c

Life of this patent

Synthesis method of avenanthramide c

Life of this patent

Abstract

Claims19