Process for the synthesis of amide bonds with the aid of novel catalysts

Patent metadata

Field	Value
Publication number	US-10544186-B2
Application number	US-201716348234-A
Country	US
Kind code	B2
Filing date	Nov 6, 2017
Priority date	Nov 9, 2016
Publication date	Jan 28, 2020
Grant date	Jan 28, 2020

Abstract

The invention relates to a process for the production of amide bonds, in particular peptide bonds, with the aid of novel amide linking reagents containing an anion of the formula (I), to the novel reagents, and to the preparation thereof.

First claim

The invention claimed is:

1. A process for production of an amide bond comprising:
reacting an acid with a primary or secondary amine in the presence of a base with the aid of at least one amide linking reagent, wherein said at least one amide linking reagent contains an anion of formula (I),
[P(C n F 2n+1 ) y F 6-y ] −   (I),

where
n stands on each occurrence, independently, for 1, 2, 3, 4, 5, 6, 7 or 8 and
y stands for 1, 2, 3 or 4.

2. The process according to claim 1 , wherein n stands on each occurrence, independently, for 2, 3 or 4.

3. The process according to claim 1 , wherein said anion of the formula (I) is selected from [(C 2 F 5 ) 3 PF 3 ] − , [(C 3 F 7 ) 3 PF 3 ] − , [(C 4 F 9 ) 3 PF 3 ] − , [(C 2 F 5 ) 2 PF 4 ] − , [(C 3 F 7 ) 2 PF 4 ] − , [(C 4 F 9 ) 2 PF 4 ] − , [(C 2 F 5 )PF 5 ] − , [(C 3 F 7 )PF 5 ] − and [(C 4 F 9 )PF 5 ] − .

4. The process according to claim 1 , wherein the cation of said at least one amide linking reagent is a uronium, thiouronium, guanidinium, aminium, carbonium, imidazolium or phosphonium cation.

5. The process according to claim 1 , wherein a peptide bond is produced.

6. A compound selected from the following group of compounds;

wherein FAP stands for an anion of the following formula (I),
[P(C n F 2n+1 ) y F 6−y ] −   (I),

where
n stands on each occurence, independently, for 1, 2, 3, 4, 5, 6, 7 or 8, and
y stands for 1, 2, 3 or 4.

7. A compound according to claim 6 , where FAP − stands for [(C 2 F 5 ) 3 PF 3 ] − or [(n-C 4 F 9 ) 3 PF 3 ] − .

Assignees

• Merck Patent Gmbh

Inventors

• Ignatyev Nikolai Mykola
• Frank Walter
• Barthen Peter
• Vysotsky Myroslav

Classifications

• C07D295/24

  Oxygen atoms · CPC title

• C07D207/263

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms · CPC title

• C07C275/06

  of an acyclic and saturated carbon skeleton · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C07C231/22

  Separation; Purification; Stabilisation; Use of additives (separation of optical isomers C07C231/20) · CPC title