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An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

Ethan A. Englund, Hosahudya N. Gopi and Daniel H. Appella*

*National Institutes of Health, 9000 Rockville Pike, Bethesda, Maryland 20892, Email: appelladniddk.nih.gov

E. A. Englund, H. N. Gopi, D. H. Appella, Org. Lett., 2004, 6, 213-215.

DOI: 10.1021/ol0361599 (free Supporting Information)


Abstract

An efficient synthesis of N(α)-Boc2-N(β)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(α)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the β-nitrogen. The success of the Curtius rearrangement depends on proper protection of the α-nitrogen.

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Key Words

Curtius Rearrangement, tert-butyl carbamates


ID: J54-Y2004-850