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Synthesis 2011(24): 4023-4026  
DOI: 10.1055/s-0031-1289586
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Preparation of α-Hydroxy-β-Fmoc Amino Acids from N-Boc Amino Acids

Erik P. Johnsona, M. Patricia Hubiekia, Andrew P. Combsb, Christopher A. Teleha*b
a J-STAR Research Inc., 3001 Hadley Road, Unit 1-3, South Plainfield, NJ 07080, USA
b Bristol-Myers Squibb Pharmaceutical Co., Pharmaceutical Research Institute, Discovery Chemistry, P.O. Box 80336, Wilmington, DE 19880, USA
Fax: +1(215)5404611; e-Mail: cteleha@its.jnj.com;
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Publication History

Received 6 September 2011
Publication Date:
03 November 2011 (online)

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Abstract

A general method for the conversion of N-Boc amino acids­ into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrolysis of the nitrile group, followed by reprotection of the amino acid as the Fmoc derivative.

Key words

N-Boc amino acid - reduction - hydrocyanation - N-Fmoc amino acid

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1

New address: Incyte Corporation, Wilmington, DE, USA.

2

New address: Johnson and Johnson Pharmaceutical Research and Development, Welsh and McKean Roads, Spring House, PA, USA.

18

Personal communication: Dr. Dan Siesel, Albany Molecular Research Inc.