TY - JOUR
T1 - Ultrasonic-assisted synthesis of two t -butoxycarbonylamino cephalosporin intermediates on SiO2
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.
UR - http://www.scopus.com/inward/record.url?scp=84985952094&partnerID=8YFLogxK
UR - https://ulrichsweb.serialssolutions.com/title/1507597941223/733546
U2 - 10.1155/2016/9734108
DO - 10.1155/2016/9734108
M3 - Article
VL - 2016
SP - 1
EP - 6
JO - Journal of Chemistry
JF - Journal of Chemistry
SN - 2090-9063
M1 - 9734108
ER -