Alkyldiphenylmethane protective agent

Patent metadata

Field	Value
Publication number	US-10870667-B2
Application number	US-201816757645-A
Country	US
Kind code	B2
Filing date	Nov 27, 2018
Priority date	Dec 19, 2017
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

Abstract

Provided is an alkyldiphenylmethane protective agent, which can prevent solidification or insolubilization of a compound by protecting a functional group of the compound to achieve easy separation and purification after a reaction.
An alkyldiphenylmethane compound represented by general formula (1):

wherein Y represents —OR 19 (wherein R 19 represents a hydrogen atom or an active ester-type protecting group), NHR 20 (wherein R 20 represents a hydrogen atom, a C 1-6 linear or branched alkyl group, or an aralkyl group), isocyanate group, an azide group, or a halogen atom, Z represents a C 1-4 linear or branched alkyl group, an alkenyl group, or a cycloalkyl group, at least one of R 1 to R 10 represents a group represented by formula (2):

and the others each independently represent a hydrogen atom, a halogen atom, a alkyl group, or a C 1-4 alkoxy group; R 11 represents a C 1-16 linear or branched alkylene group; X represents O or CONR 21 (wherein R 21 represents a hydrogen atom or a C 1-4 alkyl group); and A represents, for example, a group represented by formula (3):

wherein R 12 , R 13 , and R 14 may be the same or different and each independently represent a C 1-6 linear or branched alkyl group or an optionally substituted aryl group; R 15 represents a single bond or a C 1-3 linear or branched alkylene group; and R 16 , R 17 , and R 18 each independently represent a C 1-3 linear or branched alkylene group.

First claim

The invention claimed is:

1. An alkyldiphenylmethane compound represented by general formula (1):

wherein, Y represents —OR 19 (wherein R 9 represents a hydrogen atom or an active ester-type protecting group), —NHR 20 (wherein R 20 represents a hydrogen atom, a C 1-6 linear or branched alkyl group, or an aralkyl group), an isocyanate group, an azide group, or a halogen atom, Z represents a C 1-4 linear or branched alkyl group, an alkenyl group, or a cycloalkyl group, at least one of R 1 to R 10 represents a group represented by formula (2):

and the others each independently represent a hydrogen atom, a halogen atom, a C 1-4 alkyl group, or a C 1-4 alkoxy group; R 11 represents a C 1-16 linear or branched alkylene group; X represents O or CONR 21 (wherein R 21 represents a hydrogen atom or a C 1-4 alkyl group); and A represents a group represented by formula (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), or (13):

wherein R 12 , R 13 , and R 14 may be the same or different and each independently represent a C 1-6 linear or branched alkyl group or an optionally substituted aryl group; R 15 represents a single bond or a C 1-3 linear or branched alkylene group; and R 16 , R 17 , and R 18 each independently represent a C 1-3 linear or branched alkylene group.

2. The alkyldiphenylmethane compound according to claim 1 , wherein Y is —OR 19 (wherein R 19 represents a hydrogen atom), —NHR 20 (wherein R 20 represents a hydrogen atom, a C 1-6 linear or branched alkyl group, or an aralkyl group), or an isocyanate group.

3. The alkyldiphenylmethane compound according to claim 1 , wherein Z is a C 1-4 linear or branched alkyl group.

4. The alkyldiphenylmethane compound according to claim 1 wherein at least one of R 1 to R 5 and at least one of R 6 to R 10 are each independently a group represented by formula (2), and the others are each independently a hydrogen atom, a C 1-4 alkyl group, or a C 1-4 alkoxy group.

5. The alkyldiphenylmethane compound according to claim 1 wherein R 11 is a C 2-16 linear or branched alkylene group.

6. The alkyldiphenylmethane compound according to claim 1 wherein R 11 is a C 6-16 linear or branched alkylene group.

7. The alkyldiphenylmethane compound according to claim 1 , wherein R 15 is a single bond or a methylene group, and R 16 , R 17 , and R 18 are each independently a methylene group.

8. A method of protecting at least one of a carboxy group, a hydroxy group, an amino group, an amide group, or a mercapto group on a compound which comprises reacting the group with a compound of claim 1 .

9. The method of claim 8 wherein the compound having at least one member comprising a carboxy group, a hydroxy group, an amino group, an amide group, or a mercapto group is at least one compound selected from the group consisting of amino acids, peptides, saccharides, proteins, nucleotides.

10. The method of claim 9 the compound is a peptide.

Assignees

• Sekisui Medical Co Ltd

Inventors

• Yano Shinya
• Saito Kenta
• Kubota Hideki

Classifications

• C07K1/062

  for alpha- or omega-carboxy functions · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• Y02P20/55

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

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• C07C265/08

  the carbon skeleton containing rings · CPC title