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Photodissociable protective group

Foreign code F120006101
File No. S2008-0204
Posted date Jan 6, 2012
Country United States of America
Application number 92159709
Gazette No. 20110028738
Gazette No. 8222429
Date of filing Jan 8, 2009
Gazette Date Feb 3, 2011
Gazette Date Jul 17, 2012
International application number JP2009050102
International publication number WO2009113322
Date of international filing Jan 8, 2009
Date of international publication Sep 17, 2009
Priority data
  • P2008-061795 (Mar 11, 2008) JP
  • 2009WO-JP50102 (Jan 8, 2009) WO
Title Photodissociable protective group
Abstract (US8222429)
The present invention provides a photolabile protecting group that can be removed by light irradiation under mild conditions.
More specifically, the present invention provides a method comprising protecting a reactive functional group (e.g., a hydroxyl group, amino group, carboxyl group, carbonyl group, phosphodiester group, etc.) by the photolabile protecting group, and then removing the photolabile protecting group simply by light irradiation under neutral conditions.
The present invention relates to a compound represented by Formula (3): wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2; and a method of protecting and deprotecting an amino group etc. using the compound.
Scope of claims [claim1]
1. A compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group; and
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group.
[claim2]
2. A method of producing a compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group;
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group;
wherein the method comprises reacting a compound represented by Formula (1):
wherein Ar1, Ar2, and n are as defined above, with a compound represented by Formula (2):
wherein X are the same or different, and each represent the leaving group as defined above, or an equivalent thereof.
[claim3]
3. A method of protecting an amino group or hydroxyl group, comprising reacting the amino group or hydroxyl group with a compound represented by Formula (3):
wherein Ar1 is an optionally substituted aromatic or heteroaromatic ring, Ar2 is an optionally substituted aryl or heteroaryl group, X is a leaving group, and n is an integer of 1 or 2,
wherein the aromatic or heteroaromatic ring of Ar1 is selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a dibenzo[b,d]furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring;
wherein the optionally substituted aromatic ring Ar1 and/or the optionally substituted aryl group Ar2 has one to three substituents selected from the group consisting of an alkyl group, a haloalkyl group, an alkoxy group, a dialkylamino group, a halogen atom, a cyano group, and a nitro group; and
wherein the leaving group X is selected from the group consisting of a halogen atom, an imidazolyl group, and a pentafluorophenyl group.
  • Inventor, and Inventor/Applicant
  • SUGAWARA KAZUKI
  • GOSYO YOSHINORI
  • NARA INSTITUTE OF SCIENCE AND TECHNOLOGY
IPC(International Patent Classification)
U.S. Cl./(Sub)
  • C07D335/06
  • C07D409/04
  • C07F009/6553P60
  • C07H013/12
  • C07J033/00
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