Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

Yi Jiao Nie; Ling Li Li; Cong Liu; Rong Ji Dai; Li Quan Sun; Guo Wei Yao

Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

Yi Jiao Nie, Ling Li Li, Cong Liu, Rong Ji Dai, Li Quan Sun, Guo Wei Yao^*

^*Corresponding author for this work

School of Life Science

Beijing Institute of Technology

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

1 Citation (Scopus)

Abstract

To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by ¹H NMR, ¹³C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH ₂PO ₄ aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

Original language	English
Pages (from-to)	102-105
Number of pages	4
Journal	Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology
Volume	32
Issue number	1
Publication status	Published - Jan 2012

Keywords

Clarithromycin A
Clarithromycin A 9 oxime
Clarithromycin A(E)-9-O-methyl oxime

Cite this

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title = "Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime",

abstract = "To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.",

keywords = "Clarithromycin A, Clarithromycin A 9 oxime, Clarithromycin A(E)-9-O-methyl oxime",

author = "Nie, {Yi Jiao} and Li, {Ling Li} and Cong Liu and Dai, {Rong Ji} and Sun, {Li Quan} and Yao, {Guo Wei}",

year = "2012",

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language = "English",

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TY - JOUR

T1 - Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

AU - Nie, Yi Jiao

AU - Li, Ling Li

AU - Liu, Cong

AU - Dai, Rong Ji

AU - Sun, Li Quan

AU - Yao, Guo Wei

PY - 2012/1

Y1 - 2012/1

N2 - To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

AB - To control the commercial production of clarithromycin, clarithromycin A(E)9-O-methyl oxime was synthesized using clarithromycin A oxime as the raw material by three steps: protection of 2'-OH and 4″-OH with TMS, methylation and de-protection of TMS. The structure was identified by 1H NMR, 13C NMR and HPLC analysis was conducted. Experimental results show that the reactions are greatly affected by catalyst, solvent and pH value. The parameters of HPLC are as follows. The mobile phase is ACN/KH 2PO 4 aqueous solution (V/V=45/55), wavelength is 210 nm, temperature is 30°C and the velocity of flow is 1.0 mL/min. This synthesized compound is of benefit to control the commercial production of clarithromycin.

KW - Clarithromycin A

KW - Clarithromycin A 9 oxime

KW - Clarithromycin A(E)-9-O-methyl oxime

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M3 - Article

AN - SCOPUS:84863291761

SN - 1001-0645

VL - 32

SP - 102

EP - 105

JO - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

JF - Beijing Ligong Daxue Xuebao/Transaction of Beijing Institute of Technology

IS - 1

ER -

Synthesis and separation of the clarithromycin A(E)-9-O-methyl oxime

Abstract

Keywords

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