Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones

RM Freidinger, JS Hinkle…

Index: Freidinger, Roger M.; Hinkle, Jeffery S.; Perlow, Debra S.; Arison, Byron H. Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 77 - 81

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Citation Number: 201

Abstract

A new two-step synthesis of Fmoc-protected N-alkyl amino acids has been developed. The first step involves acid-catalyzed condensation of an Fmoc-protected amino acid with an aldehyde to form an oxazolidinone. This intermediate is then reduced with triethylsilane and trifluoroacetic acid to the N-alkylated derivative. The procedure is applicable to a variety of amino acids and aldehydes and results in less than 0.1% racemization as measured by a ...