Document Detail

On the selective N-methylation of BOC-protected amino acids.
MedLine Citation:
PMID:  19821609     Owner:  NLM     Status:  MEDLINE    
The selective N-methylation of BOC-protected valine 1a with MeI and NaH in THF (i.e., in the presence of a free carboxyl group) has been attributed to the protection of the carboxylate by chelation to Na(+). An alternative mechanism, involving the formation of the carbene intermediate generated from MeI and its insertion into the N-H bond, has been ruled out by isotopic labeling.
Andrei V Malkov; Kvetoslava Vrankov??; Miloslav Cern??; Pavel Kocovsk??
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  74     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2009 Nov 
Date Detail:
Created Date:  2009-10-30     Completed Date:  2010-01-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8425-7     Citation Subset:  IM    
Department of Chemistry, WestChem, University of Glasgow, Glasgow G12 8QQ, UK.
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MeSH Terms
Amino Acids / chemistry*
Formic Acid Esters / chemistry*
Magnetic Resonance Spectroscopy
Spectrometry, Mass, Electrospray Ionization
Reg. No./Substance:
0/Amino Acids; 0/Formic Acid Esters; 0/t-butyloxycarbonyl group

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