METHOD FOR PRODUCING AMIDE COMPOUND

• US 20200131117A1
• Filed: 04/25/2018
• Published: 04/30/2020
• Est. Priority Date: 04/25/2017
• Status: Active Grant

• Current Assignee: Chubu University Educational Foundation
• Original Assignee: Chubu University Educational Foundation
• Inventors: YAMAMOTO, Hisashi, MURAMATSU, Wataru, HATTORI, Tomohiro, SHIMODA, Yasushi
• Granted Patent: US 11,370,747 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 2531/58 Tantalum
• CPC Class Codes: B01J 31/0212 Alkoxylates
• CPC Class Codes: B01J 31/36 of vanadium, niobium or tantalum
• CPC Class Codes: C07C 231/02 from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
• CPC Class Codes: C07C 231/12 by reactions not involving the formation of carboxamide groups
• CPC Class Codes: C07C 237/12 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups peptides C07K
• CPC Class Codes: C07C 269/06 by reactions not involving the formation of carbamate groups
• CPC Class Codes: C07C 271/20 to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 271/22 to carbon atoms of hydrocarbon radicals substituted by carboxyl groups

Abstract

Provided is a novel method for producing amide compounds at high stereochemical selectivities. The method according to the present invention for producing amide compounds is provided with an amidation step for reacting, in the presence of a catalyst comprising a metal compound, an amino compound with an aminoester compound represented by general formula (1) to amidate the ester group in the aminoester compound.

Claims

1. A method for producing an amide compound, comprising an amidation step for reacting, in the presence of a catalyst comprising a metal compound, an amino compound with an aminoester compound represented by general formula (1) below to amidate the ester group in the aminoester compound:

2. The method for producing an amide compound according to claim 1, further comprising a deprotection step wherein after the amidation step, in the obtained amide compound, the protecting group PG derived from the aminoester compound represented by general formula (1) is deprotected to obtain a converted amino group.

3. The method for producing an amide compound according to claim 2, further comprising an amidation step for reacting, in the presence of a catalyst comprising a metal compound, an amide compound having the amino group obtained in claim 2 with an aminoester compound represented by general formula (1) to amidate the ester group of the aminoester compound.

4. The method for producing an amide compound according to claim 1, wherein the group PG is a tert-butoxycarbonyl group (Boc), benzyl group (Bn), benzyloxycarbonyl group (Cbz), benzoyl group (Bz), 2,2,2-trichloroethoxycarbonyl group (Troc), allyloxycarbonyl group (Alloc), 2,4-dinitrophenyl group (2,4-DNP), phthaloyl group (Phth), paramethoxy benzoyl group (PMPCO), cinnamoyl group, toluene sulfonyl group (Ts), 2- or 4-nitrobenzene sulfonyl group (Ns), or 9-fluorenyl methyloxycarbonyl group (Fmoc).

5. The method for producing an amide compound according to claim 1, wherein the amino compound is an amino compound represented by general formula (3) below:

6. The method for producing an amide compound according to claim 1, wherein the amino compound is an amino acid or a salt thereof, or an amino acid ester or a salt thereof.

7. The method for producing an amide compound according to claim 1, wherein the amount of the catalyst used is not more than 20 mol % based on 100 mol % of the aminoester compound.

8. The method for producing an amide compound according to claim 1, wherein the amidation reaction is performed in the presence of a base.

9. The method for producing an amide compound according to claim 1, wherein the amide compound obtained from the amidation reaction is represented by general formula (4) below:

10. A method for producing an amide compound, comprising an amidation step wherein, using an amino carboxylic acid compound represented by general formula (11) below and an amino compound in the presence of a catalyst comprising a metal compound, the carboxyl group of the amino carboxylic acid compound is amidated via a metal carboxylate: