New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid
Publication type: Journal Article
Publication date: 2011-03-28
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A novel and efficient procedure has been developed for the preparation of the C-7 side chain of ceftobiprole, (Z)-2-(5-amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic acid (2) from malononitrile (9) in a total yield of 19%. The key intermediate N-(3-(2-acetamido-2-oxoethyl)-1,2,4-thiadiazol-5-yl)benzamide (15b) was synthesized for the first time in 76% yield by treatment of N-(3-aminoisoxazol-5-yl)acetamide (13) with benzoyl isothiocyanate. More importantly, (Z)-N-(3-(2-acetamido-2-oxo-1-(trityloxyimino)ethyl)-1,2,4-thiadiazol-5-yl)benzamide (16b) was prepared from 15b with high stereoselectivity and good yield via successive oximation and protection of oxime hydroxy group. The process has a good prospect for industrial synthesis.
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Zhong W. et al. New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid // Organic Process Research and Development. 2011. Vol. 15. No. 3. pp. 698-703.
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Zhong W., Zhang W., Chen Y., Liu Y., Yao Y. New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid // Organic Process Research and Development. 2011. Vol. 15. No. 3. pp. 698-703.
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TY - JOUR
DO - 10.1021/op100323b
UR - https://doi.org/10.1021/op100323b
TI - New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid
T2 - Organic Process Research and Development
AU - Zhong, Weihui
AU - Zhang, Wendong
AU - Chen, Yanhui
AU - Liu, Yanbin
AU - Yao, Yi
PY - 2011
DA - 2011/03/28
PB - American Chemical Society (ACS)
SP - 698-703
IS - 3
VL - 15
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2011_Zhong,
author = {Weihui Zhong and Wendong Zhang and Yanhui Chen and Yanbin Liu and Yi Yao},
title = {New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid},
journal = {Organic Process Research and Development},
year = {2011},
volume = {15},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/op100323b},
number = {3},
pages = {698--703},
doi = {10.1021/op100323b}
}
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MLA
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Zhong, Weihui, et al. “New Procedure for the Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid.” Organic Process Research and Development, vol. 15, no. 3, Mar. 2011, pp. 698-703. https://doi.org/10.1021/op100323b.