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Facile regiospecific syntheses of N ‐α, N ‐1(τ)‐dialkyl‐l‐histidines
Author(s) -
Nayak Surendra Kumar,
Monga Vikramdeep,
Kaur Navneet,
Jain Rahul
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440607
Subject(s) - chemistry , alkyl , sodium hydride , alkylation , halide , histidine , sodium , hydride , stereochemistry , ring (chemistry) , medicinal chemistry , organic chemistry , metal , catalysis , enzyme
Two diverse methodologies describe the first synthesis of suitably protected N ‐α, N ‐1(τ)‐dialkyl‐Lhistidine derivatives. Synthesis of suitably protected N ‐α, N ‐1(τ)‐dialkyl‐L‐histidines 7‐9 containing different alkyl groups at the N ‐α and N ‐1(τ) positions was achieved in four steps starting from L‐histidine methyl ester. Whereas, in the one‐step alternate route N ‐α‐Boc‐L‐histidine methyl ester upon direct and simultaneous N ‐α and N ‐1(τ) alkylation with various alkyl halides in the presence of sodium hydride in DMF easily afforded N ‐α, N ‐1(τ)‐dialkyl‐L‐histidines 14 containing identical alkyl group at the N ‐α and N ‐1(τ) positions in high yields. Both procedures allowed facile entry to methyl and other higher alkyl groups at the N ‐α‐position of the histidine ring