A convenient synthesis of linezolid through Buchwald-Hartwig amination

Keyin Wang; Yinzhe Chen; Siyuan Wang; Qian Zhang

doi:10.1016/j.tetlet.2022.154050

A convenient synthesis of linezolid through Buchwald-Hartwig amination

Keyin Wang
, Yinzhe Chen
, Siyuan Wang
, Qian Zhang^*

^*Corresponding author for this work

Xi'an Jiaotong-Liverpool University
Suzhou Institute for Drug Control

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

A new method was developed for the synthesis of Linezolid from commercially available (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one. Linezolid is an antibiotic belongs to the family of oxazolidinones, it is successfully synthesized through a new method which include Buchwald-Hartwig amination reaction and Gabriel amine synthesis as the key steps. The synthetic route is easy to perform and with high yield. This new method provides a huge possibility for the synthesis of new linezolid derivatives that may possibly tackle the problem of bacteria resistance to oxazolidinones.

Original language	English
Article number	154050
Journal	Tetrahedron Letters
Volume	105
DOIs	https://doi.org/10.1016/j.tetlet.2022.154050
Publication status	Published - Aug 2022

Keywords

Antibiotic
BMGQMLDNAYSSOT-ZNZWXRCUSA-N
Buchwald-Hartwig reaction
Gram-positive bacteria
Linezolid
NKYJEIUMGFRATE-YGBVEIAUSA-N
OWGUMPFGBPKPRD-CNXQYKSLSA-N
Synthesis of new oxazolidinones

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10.1016/j.tetlet.2022.154050

Cite this

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title = "A convenient synthesis of linezolid through Buchwald-Hartwig amination",

abstract = "A new method was developed for the synthesis of Linezolid from commercially available (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one. Linezolid is an antibiotic belongs to the family of oxazolidinones, it is successfully synthesized through a new method which include Buchwald-Hartwig amination reaction and Gabriel amine synthesis as the key steps. The synthetic route is easy to perform and with high yield. This new method provides a huge possibility for the synthesis of new linezolid derivatives that may possibly tackle the problem of bacteria resistance to oxazolidinones.",

keywords = "Antibiotic, BMGQMLDNAYSSOT-ZNZWXRCUSA-N, Buchwald-Hartwig reaction, Gram-positive bacteria, Linezolid, NKYJEIUMGFRATE-YGBVEIAUSA-N, OWGUMPFGBPKPRD-CNXQYKSLSA-N, Synthesis of new oxazolidinones",

author = "Keyin Wang and Yinzhe Chen and Siyuan Wang and Qian Zhang",

note = "Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = aug,

doi = "10.1016/j.tetlet.2022.154050",

language = "English",

volume = "105",

journal = "Tetrahedron Letters",

issn = "0040-4039",

}

TY - JOUR

T1 - A convenient synthesis of linezolid through Buchwald-Hartwig amination

AU - Wang, Keyin

AU - Chen, Yinzhe

AU - Wang, Siyuan

AU - Zhang, Qian

PY - 2022/8

Y1 - 2022/8

N2 - A new method was developed for the synthesis of Linezolid from commercially available (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one. Linezolid is an antibiotic belongs to the family of oxazolidinones, it is successfully synthesized through a new method which include Buchwald-Hartwig amination reaction and Gabriel amine synthesis as the key steps. The synthetic route is easy to perform and with high yield. This new method provides a huge possibility for the synthesis of new linezolid derivatives that may possibly tackle the problem of bacteria resistance to oxazolidinones.

AB - A new method was developed for the synthesis of Linezolid from commercially available (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one. Linezolid is an antibiotic belongs to the family of oxazolidinones, it is successfully synthesized through a new method which include Buchwald-Hartwig amination reaction and Gabriel amine synthesis as the key steps. The synthetic route is easy to perform and with high yield. This new method provides a huge possibility for the synthesis of new linezolid derivatives that may possibly tackle the problem of bacteria resistance to oxazolidinones.

KW - Antibiotic

KW - BMGQMLDNAYSSOT-ZNZWXRCUSA-N

KW - Buchwald-Hartwig reaction

KW - Gram-positive bacteria

KW - Linezolid

KW - NKYJEIUMGFRATE-YGBVEIAUSA-N

KW - OWGUMPFGBPKPRD-CNXQYKSLSA-N

KW - Synthesis of new oxazolidinones

UR - https://www.scopus.com/pages/publications/85135936939

U2 - 10.1016/j.tetlet.2022.154050

DO - 10.1016/j.tetlet.2022.154050

M3 - Article

SN - 0040-4039

VL - 105

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154050

ER -

A convenient synthesis of linezolid through Buchwald-Hartwig amination

Abstract

Keywords

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Review of Linezolid, mechanism of action, applications, and synthesis methods. （FYP project 2022）

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A convenient synthesis of linezolid through Buchwald-Hartwig amination

Abstract

Keywords

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Other files and links

Fingerprint

Activities

Review of Linezolid, mechanism of action, applications, and synthesis methods. （FYP project 2022）

Cite this