SA-6541
Chemical Name: 3-[4-(Dimethylamino)benzylsulfanyl]-2(R)-[2(S)-methyl-3-sulfanylpropionamido]propionic acid; S-[4-(Dimethylamino)benzyl]-N-[2(S)-methyl-3-sulfanylpropionyl]-L-cysteine
CAS No. 183121-23-5
项目整合开发状态: Preclinical
项目研究机构: Santen (Originator)
合成路线:The treatment of 4-(dimethylamino)benzyl alcohol (I) with concentrated HBr at 120 C in a sealed tube provided benzyl bromide (II).This was then condensed with N-Boc-L-cysteine (III) in the presence of N,N-diisopropyl ethylamine to furnish the benzyl thioether (IV).Subsequent cleavage of the Boc group of (IV) employing HCl in dioxan yielded the intermediate aminoacid (V).
合成路线:(S)-3-Benzoylthio-2-methylpropionic acid (VI) was activated as the acid chloride (VII) by treatment with SOCl2 or optionally converted to the active ester (VIII) upon condensation with p-nitrophenol in the presence of DCC.Coupling of aminoacid (V) with either acid chloride (VII) under Schotten-Baumann conditions or with p-nitrophenyl ester (VIII) in the presence of Et3N gave rise to the corresponding amide (IX).The benzoyl thioester of (IX) was finally cleaved employing aqueous ammonia to afford the title thiol.
📌 参考资料/链接：
参考文献标题:Novel amino acid derivs.having N,N-dialkylaminophenyl group
文献作者:Kawashima,Y.; Horiuchi,M.(Santen Pharmaceutical Co.,Ltd.)
参考来源:EP 0870762; JP 1996301840; WO 9627585
📄 详细内容
合成路线:The treatment of 4-(dimethylamino)benzyl alcohol (I) with concentrated HBr at 120 C in a sealed tube provided benzyl bromide (II).This was then condensed with N-Boc-L-cysteine (III) in the presence of N,N-diisopropyl ethylamine to furnish the benzyl thioether (IV).Subsequent cleavage of the Boc group of (IV) employing HCl in dioxan yielded the intermediate aminoacid (V).
合成路线:(S)-3-Benzoylthio-2-methylpropionic acid (VI) was activated as the acid chloride (VII) by treatment with SOCl2 or optionally converted to the active ester (VIII) upon condensation with p-nitrophenol in the presence of DCC.Coupling of aminoacid (V) with either acid chloride (VII) under Schotten-Baumann conditions or with p-nitrophenyl ester (VIII) in the presence of Et3N gave rise to the corresponding amide (IX).The benzoyl thioester of (IX) was finally cleaved employing aqueous ammonia to afford the title thiol.
参考文献标题:Involvement of leukotriene B4 in murine dermatitis models
文献作者:Tsuji,F.; Miyake,Y.; Horiuchi,M.; Mita,S.
参考来源:Biochem Pharmacol 1998,55297