Journal of Organic Chemistry p. 4846 - 4855 (2019)
Update date:2022-09-26
Topics:
Li, Bryan
Li, Ruizhi
Dorff, Peter
McWilliams, J. Christopher
Guinn, Robert M.
Guinness, Steven M.
Han, Lu
Wang, Ke
Yu, Shu
The scope of thermolytic, N-Boc deprotection was studied on 26 compounds from the Pfizer compound library, representing a diverse set of structural moieties. Among these compounds, 12 substrates resulted in clean (≥95% product) deprotection, and an additional three compounds gave ≥90% product. The thermal de-Boc conditions were found to be compatible with a large number of functional groups. A combination of computational modeling, statistical analysis, and kinetic model fitting was used to support an initial, slow, and concerted proton transfer with release of isobutylene, followed by a rapid decarboxylation. A strong correlation was found to exist between the electrophilicity of the N-Boc carbonyl group and the reaction rate.
View MoreContact:027-87677569
Address:Room 2203, yujingmingmen Buidling One, xiongchu Road, wuhan city, hubei province, China
Changzhou Sunlight Pharmaceutical Co., Ltd.
Contact:+86-519-83131668;83139028;83138042;83137041
Address:JiuliStreet, Benniu Town Changzhou City, Jiangsu Province
Contact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
Shandong Yaroma Perfumery Co., Ltd.
Contact:+86- 531- 88024598
Address:7-702 Caizhi Central, 59 Gong Ye South Road, Jinan City,250101, P. R. China
Onlychem (Jinan)Biotech Co.,Ltd
Contact:86-531-83175885
Address:No. 44, Honglou South Road, Jinan,China
Doi:10.1016/0040-4020(80)80017-2
(1980)Doi:10.1016/S0040-4039(00)71511-5
(1980)Doi:10.1002/chem.201503033
(2015)Doi:10.1177/109821400002100102
(1959)Doi:10.1007/BF00777382
(1980)Doi:10.1016/j.bmcl.2004.02.033
(2004)