Sulpiride [L-(-)], Levosulpiride, RV-12309, Levopraid
(S)-(-)-舒必利Chemical Name: (S)-5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide
CAS No. 23672-07-3, 77111-58-1 (HCl)
项目整合开发状态: Launched-1987
项目研究机构: Abbott (Originator), Ravizza (Originator)
合成路线:Optically active sulpiride is prepared by converting levo-proline (I) to the correspondig levorotatory acetylproline (II),followed by reduction,chlorination and amination to afford levorotatory N-ethyl-2-aminomethylpyrrolidine (V),which,upon treatment with an ester of 2-methoxy-5-sulfamoylbenzoic acid (VI),yields N-(1-ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylbenzamide,that is,the levorotatory enantiomer of sulpiride.
📌 参考资料/链接：
参考文献标题:Levosulpiride
文献作者:Forgione,A.
参考来源:Drugs Fut 1987,12(10),944
📄 详细内容
合成路线:This compound is obtained by condensation of 2(S)-(aminomethyl)-1-ethylpyrrolidine (I) with 5-(aminosulfonyl)-2-methoxybenzoyl chloride (II) by means of K2CO3 in acetone.The starting compounds (I) and (II) are obtained as follows:a) The acylation of 2(S)-(hydroxymethyl)pyrrolidine (III) with acetic anhydride in refluxing methanol gives 1-acetyl-2(S)-(hydroxymethyl)pyrrolidine (IV),which by reaction with SOCl2 in CHCl3 is converted into 1-acetyl-2(S)-(chloromethyl)pyrrolidine (V).The reaction of (V) with sodium azide in hot DMF affords the corresponding azide (VI),which is reduced with LiAlH4 in refluxing THF to yield the desired product (I).b) The methylation of 2-hydroxybenzaldehyde (VII) with dimethyl sulfate and K2SO3 in refluxing acetone gives 2-methoxybenzaldehyde (VIII),which is oxidized with KMnO4 in hot aqueous NaOH affording 2-methoxybenzoic acid (IX).The sulfonation of (IX) with hot chlorosulfonic acid yields 5-(chlorosulfonyl)-2-methoxybenzoic acid (X),which is finally treated with 28% aqueous NaOH to give the desired product (II).
参考文献标题:Synthesis of D3-sulpiride and its (R) and (S) isomers
文献作者:Al-Koutayni-Rifai,M.; Jamet,G.; Kerr,R.R.; Jung,L.; Koffel,J.C.
参考来源:J Label Compd Radiopharm 1989,27(7),811
产品链接: CAS No. 23672-07-3›› 产品链接: CAS No.77111-58-1››