Method for producing amino acid derivatives

Patent metadata

Field	Value
Publication number	US-12202800-B2
Application number	US-202318243409-A
Country	US
Kind code	B2
Filing date	Sep 7, 2023
Priority date	Sep 21, 2018
Publication date	Jan 21, 2025
Grant date	Jan 21, 2025

Abstract

A method for producing a compound represented by the formula (1):

wherein LG is a leaving group, PG 1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s), comprising
reacting a compound represented by the formula (6):

with an amino group protecting agent to obtain a compound represented by the formula (7):

or a salt thereof;
reacting the aforementioned compound represented by the formula (7) with a lactonization agent to obtain a compound represented by the formula (8):

reacting the aforementioned compound represented by the formula (8) with an esterification agent to obtain a compound represented by the formula (9):

and
reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.

First claim

The invention claimed is:

1. A method for producing a compound represented by the formula (1):

wherein LG is a leaving group, PG 1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s),

comprising
reacting a compound represented by the formula (6):

with an amino group protecting agent to obtain a compound represented by the formula (7):

wherein each symbol is as defined above, or a salt thereof;
reacting the aforementioned compound represented by the formula (7) with a lactonization agent to obtain a compound represented by the formula (8):

wherein each symbol is as defined above;
reacting the aforementioned compound represented by the formula (8) with an esterification agent to obtain a compound represented by the formula (9):

wherein each symbol is as defined above; and
reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.

2. A method for producing a compound represented by the formula (1):

wherein LG is a leaving group, PG 1 is an amino-protecting group, and R is a hydrocarbon group having 1-8 carbon atoms and optionally having substituent(s),

comprising
reacting a compound represented by the formula (8):

wherein PG 1 is as defined above,

with an esterification agent to give a compound represented by the formula (9):

wherein each symbol is as defined above; and
reacting the aforementioned compound represented by the formula (9) with a leaving group introduction agent.

3. A compound represented by the following formula (1a) or (1b):

wherein
Boc is a tert-butoxycarbonyl group,
Ac is an acetyl group, and

Ns is a p-nitrobenzenesulfonyl group.

Assignees

• Api Corp

Inventors

• Murai Masato
• Takehara Jun
• Okado Daiki

Classifications

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• C07D211/60 Primary

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title