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

Research output: Contribution to journal › Article › Research › peer-review

40 Citations (Scopus)

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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10.1039/b206199f

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

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.",

author = "Adams, \{Luke A.\} and Cox, \{Russell J.\} and Gibson, \{Jennifer S.\} and Mayo-Mart{\'i}n, \{M. Bel{\'e}n\} and Magnus Walter and William Whittingham",

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T2 - inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase

AU - Adams, Luke A.

AU - Cox, Russell J.

AU - Gibson, Jennifer S.

AU - Mayo-Martín, M. Belén

AU - Walter, Magnus

AU - Whittingham, William

PY - 2002/1/1

Y1 - 2002/1/1

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.

UR - https://www.scopus.com/pages/publications/0036400496

U2 - 10.1039/b206199f

DO - 10.1039/b206199f

M3 - Article

AN - SCOPUS:0036400496

SN - 1359-7345

VL - 2

SP - 2004

EP - 2005

JO - Chemical Communications

JF - Chemical Communications

IS - 18

ER -

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

Abstract

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