Journal of the Chemical Society. Perkin transactions II p. 1225 - 1229 (1991)
Update date:2022-09-26
Topics:
Davis, Andrew M.
Layland, Nicola J.
Page, Michael I.
Martin, Frances
O'Ferrall, Rory More
The alkaline hydrolysis of (3S,5R,6R)-methyl benzylpenicilloate, and the corresponding carboxamide and N-ethylamide, is accompanied by an absorbance increase at 285 nm.This is attributed to a competing elimination reaction across C6-C5 to open the thiazolidine ring and reversibly generate an enamine intermediate.Kinetic analysis and hydrolysis in D2O do not indicate a significant buildup of this intermediate during hydrolysis of the methyl ester.However, over the pH range 4-11 the rate of thiazolidine ring opening is competitive with hydrolysis of the ester function.The deuterium solvent kinetic isotope effect on the ring closure reaction is 7.5.
View MoreKAIYUAN CHEMICAL COMPANY LIMITED.
website:http://www.kaiyuanchem.com
Contact:+86-22-59891255/66/77
Address:B-2205, Kuangshi International Building, Yingbin Road, XiangLuo Bay Business District, Binhai New area, Tianjin, China.
Contact:+86-021-50792271
Address:Building 24A, 300 Chuantu Road, Chuansha, Pudong new area, Shanghai, China, 201202
Tianjin Emulsion Science&Technology Development Co.,Ltd
Contact:13901380442
Address:Vake Garden New Town New Yi Bai Road Beichen District Tianjin,China
Changzhou Kingyo Chemical Corporation Ltd.
website:http://www.kingyochem.com
Contact:+86-519-85105717
Address:19# Wuqing North Road, Changzhou , Jiangsu, China
Contact:Tel:+86-29-88764861 Fax:+86-29-88764861
Address:Rm#2107, Block A, Epin Meidao Building, Gaoxin Rd, Hi-Tech Zone, Xi’an, China
Doi:10.1016/j.catcom.2016.02.007
(2016)Doi:10.1002/hlca.19780610509
(1978)Doi:10.1016/S0968-0896(02)00643-0
(2003)Doi:10.1007/s11172-007-0169-y
(2007)Doi:10.1016/0040-4020(95)00396-P
(1995)Doi:10.1139/v73-386
(1973)
