Chemical and Pharmaceutical Bulletin p. 877 - 882 (1994)
Update date:2022-08-03
Topics:
Morie
Kato
Harada
Yoshida
Matsumoto
The enantiomers, (S)-(-)-1 and (R)-(+)-1, of (+)-4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]met hyl]benzamide (mosapride) [(+)-1], a new and selective gastroprokinetic agent, were prepared from optically active [4-(4-fluorobenzyl)-2-morpholinyl]methylamines (S)-(-)-4 and (R)-(+)-4, respectively. The requisite (S)-(-)-4 and (R)-(+)-4 were prepared by optical resolution of [4-(4-fluorobenzyl)-2-morpholinyl]methyl p-toluenesulfonate [(+)-5] using (-)- and (+)-N-(p-toluenesulfonyl)glutamic acids, followed by amination of the tosyloxy groupe of (R)-(-)-5 and (S)-(+)-5, respectively. The absolute configurations of (R)-(-)-5 and (S)-(+)-5 were determined on the basis of an asymmetric synthesis of (R)-(-)-5 from (S)-(+)-benzyl glycidyl ether [(S)-(+)-11]. Mosapride and its enantiomers, (S)-(-)-1 and (R)-(+)-1, were essentially equipotent in serotonin 5-HT4 receptor agonistic activity on the electrically evoked contractions in isolated guinea pig ileum.
View MoreSuzhou Howsine Biological Technology Co.,Ltd(expird)
website:http://www.howsine.com
Contact:86-512-67262751
Address:No 3,Weihua Road ,Suzhou Industrial Park ,Jiangsu ,China.
Guangxi Shanyun Biochemical Science and Technology Co., Ltd
Contact:+86-0772--6828887
Address:#2 Industrial Park of Luzhai County, Liuzhou, Guangxi, China
website:http://www.shtopchem.com/
Contact:0086-0576-87776998
Address:room no 1608,xuhui business building yude road,xujiahui street, xuhui district
Nanjing Chemipioneer Pharma&Tech Co.,Ltd
website:http://www.chemipioneer.com.cn
Contact:+86-25-52685700
Address:Room 305,A Block,Biological-Medicine Building,Business Start-up Center,Xin-ke 1st Road, High-tech development zone,Nanjing city,Jiangsu Province, China
Golden Union Agrochemical Import and Export Co., Ltd.
Contact:86-755-23910527
Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
Doi:10.1016/0039-128X(67)90115-8
(1967)Doi:10.1002/anie.201304096
(2013)Doi:10.1055/s-1993-25832
(1993)Doi:10.1021/jo402010b
(2013)Doi:10.1063/1.1696756
(1965)Doi:10.1021/jo00117a057
(1995)