Ultrasonic-assisted synthesis of two t -butoxycarbonylamino cephalosporin intermediates on SiO2

Feng Xue; Yibin Wei; Shengui Ju; Weihong Xing

doi:10.1155/2016/9734108

Ultrasonic-assisted synthesis of two t -butoxycarbonylamino cephalosporin intermediates on SiO₂

Feng Xue, Yibin Wei, Shengui Ju^*, Weihong Xing

^*Corresponding author for this work

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Abstract

Herein, we describe a facile and high efficient strategy for the synthesis of two forms of the 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylates using ultrasonic irradiation. By SiO₂ as weak Lewis acid catalyst, 4-methoxybenzyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-carboxylate (Boc-ACLE) and benzhydryl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (Boc-ACLH) were successfully synthesized through the efficient protection of the N-t-butoxycarbonyl (N-Boc), and the reactions occurred at low temperature requiring short reaction times and exhibiting excellent isolated yields (96% and 96.2%, resp.). The advantages of this reaction route including the usage of economical reagents and mild reaction conditions and high isolated yield make the two significant t-butoxycarbonylamino cephalosporin intermediates possible in large-scale production.

Original language	English
Article number	9734108
Pages (from-to)	1-6
Number of pages	6
Journal	Journal of Chemistry
Volume	2016
DOIs	https://doi.org/10.1155/2016/9734108
Publication status	Published - 2016

Bibliographical note

Copyright the Author(s) 2016. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

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10.1155/2016/9734108

Publisher version (open access)Final published version, 256 KBLicence: CC BY

Cite this

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title = "Ultrasonic-assisted synthesis of two t -butoxycarbonylamino cephalosporin intermediates on SiO2",

abstract = "Herein, we describe a facile and high efficient strategy for the synthesis of two forms of the 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylates using ultrasonic irradiation. By SiO2 as weak Lewis acid catalyst, 4-methoxybenzyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-carboxylate (Boc-ACLE) and benzhydryl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (Boc-ACLH) were successfully synthesized through the efficient protection of the N-t-butoxycarbonyl (N-Boc), and the reactions occurred at low temperature requiring short reaction times and exhibiting excellent isolated yields (96% and 96.2%, resp.). The advantages of this reaction route including the usage of economical reagents and mild reaction conditions and high isolated yield make the two significant t-butoxycarbonylamino cephalosporin intermediates possible in large-scale production.",

author = "Feng Xue and Yibin Wei and Shengui Ju and Weihong Xing",

note = "Copyright the Author(s) 2016. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.",

year = "2016",

doi = "10.1155/2016/9734108",

language = "English",

volume = "2016",

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AU - Xue, Feng

AU - Wei, Yibin

AU - Ju, Shengui

AU - Xing, Weihong

N1 - Copyright the Author(s) 2016. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

PY - 2016

Y1 - 2016

N2 - Herein, we describe a facile and high efficient strategy for the synthesis of two forms of the 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylates using ultrasonic irradiation. By SiO2 as weak Lewis acid catalyst, 4-methoxybenzyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-carboxylate (Boc-ACLE) and benzhydryl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (Boc-ACLH) were successfully synthesized through the efficient protection of the N-t-butoxycarbonyl (N-Boc), and the reactions occurred at low temperature requiring short reaction times and exhibiting excellent isolated yields (96% and 96.2%, resp.). The advantages of this reaction route including the usage of economical reagents and mild reaction conditions and high isolated yield make the two significant t-butoxycarbonylamino cephalosporin intermediates possible in large-scale production.

AB - Herein, we describe a facile and high efficient strategy for the synthesis of two forms of the 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylates using ultrasonic irradiation. By SiO2 as weak Lewis acid catalyst, 4-methoxybenzyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-carboxylate (Boc-ACLE) and benzhydryl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (Boc-ACLH) were successfully synthesized through the efficient protection of the N-t-butoxycarbonyl (N-Boc), and the reactions occurred at low temperature requiring short reaction times and exhibiting excellent isolated yields (96% and 96.2%, resp.). The advantages of this reaction route including the usage of economical reagents and mild reaction conditions and high isolated yield make the two significant t-butoxycarbonylamino cephalosporin intermediates possible in large-scale production.

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