Spirodiamino Acid Scaffold for Combinatorial Synthesis

Patent Spirodiamino Acid Scaffold for Combinatorial Synthesis 

Dolle etal, US Patent 6,175,020 (January 16, 2001) Assignee Pharmacopeia, Inc. 

Utility Template for Synthetic Receptor and Enzyme Intermediates 

A solution of ethyl 2,10-di-ene-6-keto-undecanoic acid (3.30 mmol) and t-butylcarbazate in 10 ml diethyl ether was stirred at ambient temperature overnight and the resulting white precipitate isolated by filtration in 97% yield, mp = 103-105°C. H-NMR, IR, and elemental analysis data supplied. 

The product from Step 1 (34.21 mmol) was dissolved in 25% TEA in CH2CI2, stirred for 1 hour, concentrated, and the residual dissolved in 100 ml 1M HCl in methyl alcohol. To this was added Pt02 (4.41 mmol) and the mixture hydrogenated at 80 psi overnight. 

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