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Amination of Aryl Alcohol Derivatives

详细技术说明

None

*Abstract

Recently, researchers in the laboratory of Dr. Neil Garg, of the Department of Chemistry & Biochemistry at UCLA, have completed the first amination reactions of aryl O-sulfamates. In addition, the researchers have discovered that aryl carbamates are also excellent substrates for Ni-catalyzed amination reactions. Though relatively unexplored, these electrophilic cross-coupling partners possess a number of benefits compared to more conventional phenol based electrophiles. They are easy to prepare, exhibit pronounced stability to a variety of reaction conditions, show low reactivity toward Pd(0), and are able to direct ortho metalation. In combination, these characteristics make aryl O-sulfamates and aryl O-carbamates ideal partners for the multistep synthesis of polysubstituted aromatics. Applying this novel amination methodology, UCLA researchers were able to derive a concise synthesis of the antibacterial drug linezolid.

*IP Issue Date

Feb 14, 2017

*Principal Investigation

Name: Neil Garg

Department:

Name: Kyle Quasdorf

Department:

Name: Stephen Ramgren

Department:

Name: Amanda Silberstein

Department:

附加资料

Patent Number: US20130289270A1
Application Number: US13978384A
Inventor: Garg, Neil K. | Ramgren, Stephen D. | Silberstein, Amanda L. | Quasdorf, Kyle W.
Priority Date: 7 Jan 2011
Priority Number: US20130289270A1
Application Date: 3 Jul 2013
Publication Date: 31 Oct 2013
IPC Current: C07D026338 | C07D020908 | C07D021106 | C07D021374 | C07D0295033 | C07D0295073 | C07D0295096 | C07F000710
US Class: 544069 | 544124 | 544137 | 544143 | 544174 | 544178 | 544360 | 546192
Assignee Applicant: The Regents of the University of California
Title: Amination of Aryl Alcohol Derivatives
Usefulness: Amination of Aryl Alcohol Derivatives
Summary: For preparing cross coupled compound used as an intermediate in synthesis of linezolid (claimed).
Novelty: Making cross-coupled compound used as an intermediate in synthesis of linezolid involves combining aryl alcohol derivative containing aryl carbamate compound, amine, and transition metal catalyst containing nickel or palladium

主要类别

化工/材料

细分类别

化工/材料应用

申请号码

9567307

其他

Background

Transition metal-catalyzed amination reactions are amongst the most powerful methods available for accessing the carbon nitrogen based motifs ubiquitously found in medicinal agents and natural products. Recently, efforts have focused on the amination of classically “inert” simple phenolic derivatives to synthesize these structures more readily. Towards this goal, a number of groups have searched for alternative phenol based amination partners, which can be used to direct the assembly of functional groups onto an aromatic ring. Resulting polysubstituted aryl amine motifs are commonly encountered in drug scaffolds, naturally occurring small molecules, pesticides, ligands for catalysis, and materials chemistry. Given the ubiquity of carbon-nitrogen bonds in medicinal agents, more efficient and cost-effective cross-coupling reactions will provide significant economic advantages to therapeutic development and manufacturing.

Related Materials

Nickel-catalyzed cross-couplings involving carbon-oxygen bonds. Chem Rev. (2011)
Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst. Org Lett. (2012)
Nickel-catalyzed amination of aryl sulfamates. Angew Chem Int Ed Engl. (2011)
Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings. Chem. Sci. (2011)

Additional Technologies by these Inventors

• Cross Coupling of Phenolic Derivatives

Tech ID/UC Case

22255/2011-248-0

Related Cases

2011-248-0

国家/地区

美国