| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5226062 | Tetrahedron | 2009 | 7 Pages |
Abstract
A practical synthesis of (2R,3S)- and (2S,3R)-β-methyltryptophan ethyl ester (β-MeTrp-OEt) has been developed. Racemic threo-β-MeTrp-OEt was diastereoselectively prepared via crystallization-induced diastereomer transformation (CIDT) of the α-nitro equivalent of β-MeTrp-OEt. The enantiomers were resolved via diastereomeric salt formation using a half equivalent of (R)-2-(4-hydroxyphenoxy)propionic acid. The process allowed a diabetes drug candidate N-[(1R,2S)-1-({5-[(dimethylamino)methyl]-2-ethoxyphenyl}aminocarbonyl)-2-(1H-indol-3-yl)propyl]-4-phenyl-1-piperidinecarboxamide to be prepared in good yield with high quality.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Yasuhiro Sawai, Masahiro Mizuno, Tatsuya Ito, Jun-ichi Kawakami, Mitsuhisa Yamano,