Efficient synthesis of an imidazole-substituted delta-amino acid by the integration of chiral technologies |
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Authors: | Appleby Ian Boulton Lee T Cobley Christopher J Hill Catherine Hughes Mike L de Koning Pieter D Lennon Ian C Praquin Céline Ramsden James A Samuel Helen J Willis Niamh |
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Institution: | Dowpharma, Chirotech Technology, Ltd., A Subsidiary of The Dow Chemical Company, Cambridge, UK. |
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Abstract: | Two methods to produce (2S)-5-amino-2-(1-n-propyl-1H-imidazol-4-ylmethyl)-pentanoic acid were investigated. Diastereoisomeric salt resolution, using the quinidine salt, gave the desired intermediate in 98% ee and 33% yield. Asymmetric hydrogenation of various substrates gave high conversions, with up to 83% ee. Integration of these two approaches via asymmetric hydrogenation of a quinidine salt substrate followed by crystallization provided the desired intermediate in 94% ee and 76% yield. |
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