NDLI: Mild and convenient N-formylation protocol in water-containing solvents

Content Provider	PubMed Central
Author	Aleiwi, Bilal A. Mitachi, Katsuhiko Kurosu, Michio
Copyright Year	2009
Abstract	We have realized that N-formylations of free amines of some drug leads can improve PK/PD property of parent molecules without decreasing their biological activities. In order to selectively formylate primary amines of polyfunctional molecules, we have sought a mild and convenient formylation reaction. In our screening of N-formylation of an α-amino acid, L-phenylalanine, none of formylation conditions reported to date yielded the desired HCO-L-Phe-OH with satisfactory yield. N-Formylations of amino acids with HCO2H require the reactions in a water-containing media and suppress polymerization reactions due to the competitive reactions among carboxylic acids. We found that N-formylations of α-amino acids could be achieved with a water-soluble peptide coupling additive, an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-cyano-2-(hydroxyimino)acetate (2), EDCI, and NaHCO3 in water or a mixture of water and DMF system, yielding N-formylated α-amino acids with excellent yields. Moreover, these conditions could selectively formylate primary amines over secondary amines at a controlled temperature. A usefulness of these conditions was demonstrated by selective formylation of daptomycin antibiotic which contains three different amino groups.
Related Links	http://dx.doi.org/10.1016/j.tetlet.2013.02.013
Ending Page	2081
Page Count	5
Starting Page	2077
File Format	PDF
ISSN	00404039
Journal	Tetrahedron letters
Issue Number	16
Volume Number	54
Language	English
Publisher Date	2013-04-01
Access Restriction	Open
Subject Keyword	Organic Chemistry Biochemistry Drug Discovery Research in Higher Education
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Drug Discovery Biochemistry

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