A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase

Luke A. Adams; Russell J. Cox; Jennifer S. Gibson; M. Belén Mayo-Martín; Magnus Walter; William Whittingham

doi:10.1039/b206199f

A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase

Luke A. Adams, Russell J. Cox, Jennifer S. Gibson, M. Belén Mayo-Martín, Magnus Walter, William Whittingham

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Abstract

A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNHP(O)(OEt)₂ in situ—the methodology is especially suited to acid sensitive systems featuring BOC,^tBu or acetal protecting groups.

Original language	English
Pages (from-to)	2004-2005
Number of pages	2
Journal	Chemical Communications
Volume	2
Issue number	18
DOIs	https://doi.org/10.1039/b206199f
Publication status	Published - 1 Jan 2002
Externally published	Yes

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abstract = "A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNHP(O)(OEt)2 in situ—the methodology is especially suited to acid sensitive systems featuring BOC,tBu or acetal protecting groups.",

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AU - Adams, Luke A.

AU - Cox, Russell J.

AU - Gibson, Jennifer S.

AU - Mayo-Martín, M. Belén

AU - Walter, Magnus

AU - Whittingham, William

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N2 - A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNHP(O)(OEt)2 in situ—the methodology is especially suited to acid sensitive systems featuring BOC,tBu or acetal protecting groups.

AB - A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNHP(O)(OEt)2 in situ—the methodology is especially suited to acid sensitive systems featuring BOC,tBu or acetal protecting groups.

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JO - Chemical Communications

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A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase

Abstract

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