Chemical and Pharmaceutical Bulletin p. 146 - 150 (1999)
Update date:2022-08-03
Topics:
Yamada, Shin-ichi
Tsujioka, Ikuko
Shibatani, Takeji
Yoshioka, Ryuzo
An effective new route to diltiazem, a representative coronary vasodilator, through (-)-(2R,3S)-3-(4-methoxyphenyl)glycidamide [(-)-2] has been achieved. The glycidamide (-)-2 was prepared in 43% overall yield by a combination of the enzymatic resolution of methyl (±)2(2RS,3SR)-3-(4- methoxyphenyl)glycidate [(±)-1] with lipase and the following amidation of (-)-1 with ammonia. A one-pot synthesis through the treatment of (-)-2 with 2-aminothiophenol and a following ring closing reaction efficiently gave a key intermediate of diltiazem synthesis, (2S,3S)-2,3-dihydro-3-hydroxy-2-(4- methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [cis-(+)-5] in 80% overall yield.
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Doi:10.1039/a807567k
(1999)Doi:10.1021/jf980347+
(1999)Doi:10.1134/S1070363206060120
(2006)Doi:10.1134/S1070363218090232
(2018)Doi:10.1016/j.tet.2012.02.043
(2012)Doi:10.1016/S0040-4039(00)89545-3
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