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ChemInform Abstract: A Stereospecific Synthesis of Both Enantiomers of 2-(1′-Amino-2′- methylpropyl)imidazole, a Key Synthon in the Synthesis of SB 203386; a Potent Protease Inhibitor.

✍ Scribed by L. N. PRIDGEN; M. K. MOKHALLALATI; M. A. MCGUIRE

Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

A Stereospecific Synthesis of Both Enantiomers of 2-(1'-Amino-2'methylpropyl)imidazole, a Key Synthon in the Synthesis of SB 203386; a Potent Protease Inhibitor. -Two different diastereospecific approaches to chiral 2-(1-amino-2-methylpropyl)imidazoles (VI), parts of the inhibitor (VII), are developed. The first route utilizes the nucleophilic addition of an isopropyl cerium reagent to the oxazolidine (III). The second route avoids the expensive starting material (I) and allows access to (R)-and (S)-(VI) using the corresponding substrate (IX). -(PRIDGEN, L. N.; MOKHALLALATI,

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