# US 11,897,844 B2 · Method for producing amino acid derivatives

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,897,844 B2
- Document ID: US11897844B2
- Status: Granted
- Kind: B2
- Application number: 17/277,456
- Filed: 2019-09-24
- Published: 2021-12-30
- Granted: 2024-02-13
- Earliest claimed: 2018-09-21
- Assignees: Api Corporation
- Applicants: Api Corporation
- Inventors: Masato Murai; Jun Takehara; Daiki Okado
- Web page: https://patentgrep.com/patent/US11897844B2

## CPC

- C07D 211/60: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention aims to provide a method for producing a (2S,5R)-5-(protected oxyamino)-piperidine-2-carboxylic acid derivative at a low cost that can be performed under mild reaction conditions not requiring a facility at an extremely low temperature, is safer, can control the quality of the desired product with ease, and shows good workability in the site of production. A method for producing a compound represented by the formula (2): wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), including a step of reacting a compound represented by the formula (1): wherein each symbol is as defined above, with a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above, in the presence of a base in a solvent.

## Claims

### Claim 1

A method for producing a compound represented by the formula (2):
wherein PG1 is an amino-protecting group, PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, LG is a leaving group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), wherein the leaving group is a sulfonyloxy group,
comprising
reacting
a compound represented by the formula (1):
wherein each symbol is as defined above, with
a hydroxylamine derivative represented by the formula PG2NHOPG3 wherein each symbol is as defined above in the presence of a base in a solvent.

### Claim 2 (depends on 1)

The production method according to claim 1, wherein PG1 is a carbamate type protecting group or an amide type protecting group, and a σp− value thereof is not more than 1.00.

### Claim 3 (depends on 1)

The production method according to claim 1,
wherein the compound represented by the formula (1) and the hydroxylamine derivative represented by the formula:PG2NHOPG3 wherein PG2 is an amino-protecting group, PG3 is a hydroxyl-protecting group, and other symbols are each as defined above, are reacted at 10° C. -70° C.