Method for producing amino acid aminoalkyl ester or inorganic acid salt thereof

Patent metadata

Field	Value
Publication number	US-11827586-B2
Application number	US-201917052541-A
Country	US
Kind code	B2
Filing date	May 15, 2019
Priority date	May 15, 2018
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

The present invention provides a method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof.

First claim

The invention claimed is:

1. A method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting:
a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and
at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof:

wherein in general formula (I), R 11 represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms which may have a substituent; the substituent is a group selected from the group consisting of monovalent aliphatic hydrocarbon groups having at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups having at least 6 but not more than 10 carbon atoms, groups represented by general formula (II-1) shown below and groups represented by general formula (II-2) shown below; R 12 represents a group selected from the group consisting of groups represented by general formula (II-1) shown below and groups represented by general formula (II-2) shown below; R 13 represents a hydrogen atom; and n11 is 1,

wherein in general formula (II-1), R 21 represents a monovalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms which may have a substituent; and
in general formula (II-2), R 22 represents a monovalent organic group;

wherein in general formula (III), n31 is an integer of at least 2 but not more than 4; R 31 represents an n31-valent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms which may have a substituent, or an n31-valent aromatic cyclic group having at least 6 but not more than 10 carbon atoms which may have a substituent; the substituent is a group selected from the group consisting of monovalent aliphatic hydrocarbon groups having at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups having at least 6 but not more than 10 carbon atoms, groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4); R 32 represents a group selected from the group consisting of groups represented by the general formula (II-1), groups represented by the general formula (II-2) and groups represented by the general formula (II-3); and R 33 represents a hydrogen atom or a monovalent organic group,

wherein in general formula (II-3), each of R 23 and R 24 independently represents a monovalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms which may have a substituent; and

wherein in general formula (II-4), R 25 represents a hydrogen atom or a monovalent organic group,

wherein in general formula (IV-I), Y 401 represents a divalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms; and R 401 represents a group selected from the group consisting of an amino group, —NHCONH 2 , groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3),

wherein in general formula (IV-II), each of Y 402 and Y 403 independently represents a divalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms; and each of R 402 and R 403 independently represents a group selected from the group consisting of a hydrogen, an amino group, —NHCONH 2 , groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3), provided that R 402 and R 403 do not simultaneously represent a hydrogen,

wherein in general formula (IV-III), each of Y 404 , Y 405 and Y 406 independently represents a divalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms; and each of R 404 , R 405 and R 406 independently represents at I act one a group selected from the group consisting of a hydrogen, an amino group, —NHCONH 2 , groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3), provided that R 404 , R 405 and R 406 do not simultaneously represent a hydrogen,

wherein in general formula (IV-IV), each of Y 407 , Y 408 , Y 409 and Y 4010 represents a divalent aliphatic hydrocarbon group having at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group having at least 6 but not more than 10 carbon atoms; at least one of R 407 , R 408 , R 409 and R 4010 represents a hydroxyl group, and each of the others represents a group selected from the group consisting of a hydrogen, an amino group, —NHCONH 2 , groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3), provided that R 407 , R 408 , R 409 and R 4010 do not simultaneously represent a hydrogen,
wherein the reaction is conducted in presence of at least one acid catalyst selected from the group consisting of organic acids and inorganic acids having a normal boiling point of 0° C. or higher, and
the inorganic acid used as an acid catalyst is at least one acid selected from the group consisting of sulfuric acid, phosphoric acid, nitric acid and boric acid.

2. The method according to claim 1 , wherein the salt of the compound represented by general formula (I) or general formula (III) is obtained from an acid, which is the same as the acid catalyst.

3. The method according to claim 1 , wherein the compound represented by general formula (I) or the compound represented by general formula (III), or a salt thereof, is reacted with the compound represented by general formula (IV-I) or an inorganic acid salt thereof.

4. The method according to claim 3 , wherein
in the general formula (I):
R 11 represents a hydrogen atom or a monova

Assignees

• Asahi Chemical Ind

Inventors

• Miyake Nobuhisa
• Takagaki Kazuhiro
• UEMATSU Tsubasa
• Nakaoka Koichi
• Shinohata Masaaki

Classifications

• C07C269/06 Primary

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

• C07C227/18

  by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters · CPC title

• C07C249/02

  of compounds containing imino groups · CPC title

• C07C273/18

  of substituted ureas · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title