Agent for introducing protecting group for hydroxy group and/or mercapto group

Patent metadata

Field	Value
Publication number	US-10160694-B2
Application number	US-201515517899-A
Country	US
Kind code	B2
Filing date	Sep 30, 2015
Priority date	Oct 7, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A novel agent for introducing a protecting group for a hydroxy group and/or a mercapto group that can be introduced and removed under mild conditions is provided. The agent for introducing a protecting group for a hydroxy group and/or mercapto group of a substrate compound having the hydroxy group and/or mercapto group is represented by the following formula (I), wherein A represents a ring structure having 1 to 5 rings in which two carbon atoms of an adjacent benzene ring are included, the ring structure comprises a substituted or unsubstituted five-membered ring or six-membered ring and optionally include a heterocycle; each of R 1 , R 2 , R 3 , and R 4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO 2 R 5 (R 5 =an aryl group or an alkyl group).

First claim

The invention claimed is:

1. An agent for introducing a protecting group for a hydroxy group and/or a mercapto group of a substrate compound having the hydroxy group and/or mercapto group, being represented by the following formula (I):

wherein A is a benzene ring, a pyridine ring, a thiophene ring, a pyrrole ring, a naphthalene ring, or an anthracene ring; each of R 1 , R 2 , R 3 , and R 4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

2. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 ,
wherein the agent is represented by any of the following formulas (I)-1 to (I)-6:

wherein each of R 1 , one or more R 2 , R 3 , and R 4 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms; and X is a halogen atom or OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

3. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 , wherein
the hydroxy group and/or mercapto group contained in the substrate compound are protected by reacting the substrate compound with a compound represented by the formula (I) in coexistence of a base in a reaction.

4. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 3 , wherein
the reaction is performed by adding a base represented by the following formula (II)-1 or formula (II)-2:

wherein each of R 6 and R 7 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms.

5. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 ,
being represented by the following formula (I)-a:

wherein X is a halogen atom or OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

6. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 5 ,
wherein the agent is represented by any of the following formulas (I)-a-1 to (I)-a-4:

7. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 , wherein X is a halogen atom.

8. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 , wherein X is OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

9. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 2 , wherein X is a halogen atom.

10. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 2 , wherein X is OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

11. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 5 , wherein X is a halogen atom.

12. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 5 , wherein X is OSO 2 R 5 , wherein R 5 is an alkyl group, a phenyl group, or a tolyl group.

13. The agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 , wherein the reaction is performed in the presence of a solvent, wherein the solvent is toluene.

14. A method for introducing a protecting group for a hydroxy group and/or a mercapto group of a substrate compound, the method comprising reacting the substrate compound with the agent for introducing a protecting group for a hydroxy group and/or a mercapto group according to claim 1 in a reaction.

15. The method according to claim 14 , wherein the reaction is performed in coexistence of a base.

16. The method according to claim 15 , wherein the reaction is performed by adding a base represented by the following formula (II)-1 or formula (II)-2:

wherein each of R 6 and R 7 is independently a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms.

Assignees

• Univ Kyushu Nat Univ Corp

Inventors

• TORIKAI Kohei

Classifications

• C07C41/16

  by reaction of esters of mineral or organic acids with hydroxy or O-metal groups · CPC title

• C07B41/02 Primary

  of hydroxy or O-metal groups · CPC title

• C07C309/63

  Esters of sulfonic acids · CPC title

• C07D333/72

  Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes · CPC title

• C07D215/02

  having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom · CPC title