(Cyanomethylene) phosphoranes as carbonyl 1,1-dipole synthons fo

Details (Cyanomethylene) phosphoranes as carbonyl 1,1-dipole synthons fo (Cyanomethylene) phosphoranes as carbonyl 1,1-dipole synthons fo

1995-07-14

1998-11-10

Tsang, Cecilia J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530333, 530338, 568 9, C07K 102, C07F 9535

Patent

active

058345884

ABSTRACT:
The invention is directed to systematic synthetic and testing strategies for .alpha.-keto acids, esters and amides. The method of synthesis comprises (A) reacting (cyanomethylene)triphenylphosphorane with a carbonyl compound selected from carboxylic acids (RCOOH) and acyl chlorides (RCOCl) to make a cyano keto phosphorane, (B) oxidizing said phosphorane and (C) reacting the oxidized product with a nucleophile (NuH) to make the product .alpha.-keto acid, ester or amide. Systematic synthesis and testing are achieved by a modular approach in which arrays of molecules are generated by variation of R and Nu.

REFERENCES:
"Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of .alpha.-Keto Acids, Esters, and Amides", Harry H. Wasserman and Wen-Bin Ho, J. Organic Chemistry, 1994, 59, 4364-4366.
Wasserman et al, J. Org. Chem., 58 (18), 4785-4787, 1993), Sep. 1993.

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