# US 2025/0353815 A1 · AMINO ACID HAVING FLUORINE AT a-POSITION, AND DERIVATIVE OF SAME

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- Number: US 2025/0353815 A1
- Document ID: US20250353815A1
- Status: Published application
- Kind: A1
- Application number: 18/873,930
- Filed: 2023-06-16
- Published: 2025-11-20
- Earliest claimed: 2022-06-17
- Assignees: SynCrest Inc.; University of the Ryukyus
- Applicants: SynCrest Inc.; University of the Ryukyus
- Inventors: Pengyu XU; Shin YONEYAMA; Satoru ARIMITSU; Riko GENKA
- Web page: https://patentgrep.com/patent/US20250353815A1

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07B 39/00: Halogenation
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A first object of the present invention is to provide an amino acid compound having the α-position fluorinated by fluorinating the α-position with high yields. A second object of the present invention is to provide an amino acid compound having the α-position fluorinated by fluorinating the α-position with high enantioselectivity. Provided are amino acids having fluorine at the α-position and their derivatives.

## Claims

### Claim 1

A fluorinated amino acid compound represented by formula (1):
wherein
R represents an alkyl group, an alkoxy group, an aryl group, an ester group, an aralkyl group, an alkenyl group, or an alkynyl group, and
Nphth represents an N-phthaloyl group:

### Claim 2

A method for producing a fluorinated amino acid compound represented by formula (2):
wherein
R represents an alkyl group, an alkoxy group, an aryl group, an ester group, an aralkyl group, an alkenyl group, or an alkynyl group, and
Nphth represents an N-phthaloyl group:
the method comprising mixing a compound represented by formula (3):
wherein R and Nphth are as defined in formula (1) above
with a fluorinating agent in an organic solvent in presence of a catalyst to fluorinate an α-position of the compound represented by formula (3).

### Claim 3 (depends on 2)

The method according to claim 2, wherein the organic solvent is at least one organic solvent selected from the group consisting of nitrile solvents, nitro solvents, alcohol solvents, halogen solvents, ether solvents, ester solvents, hydrocarbon solvents, and aromatic solvents.

### Claim 4 (depends on 2)

The method according to claim 2, wherein the catalyst is an amine compound.

### Claim 5 (depends on 2)

The method according to claim 2, wherein the fluorinating agent is at least one fluorinating agent selected from the group consisting of N-fluorobenzenesulfonimide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate, 2,6-dichloro-1-fluoropyridinium tetrafluoroborate, and 2,6-dichloro-1-fluoropyridinium triflate.

### Claim 6 (depends on 4)

The method according to claim 4, wherein the fluorinating agent is at least one fluorinating agent selected from the group consisting of N-fluorobenzenesulfonimide, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis (tetrafluoroborate), 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate, 2,6-dichloro-1-fluoropyridinium tetrafluoroborate, and 2,6-dichloro-1-fluoropyridinium triflate.