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The Synthesis of p ‐Methoxybenzyloxycarbonyl Amino Acids
Author(s) -
Chen ShuiTein,
Weng ChihShyong,
Wang KungTsung
Publication year - 1987
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198700018
Subject(s) - chemistry , phosgene , oxime , residue (chemistry) , amino acid , lysine , organic chemistry , medicinal chemistry , biochemistry
o ‐Chlorobenzyloxycarbonylimino‐2‐phenylacetonitrile (Cl‐Z‐ON) and p ‐methoxybenzyloxycarbonylimino‐2‐phenylacetonitrile (MOZ‐ON) have been prepared from 2‐hydroxyimino‐2‐phenylacetonitrile (oxime), phosgene, and the corresponding alcohols. Cl‐Z‐ON is synthesized for the first time and found to be stable at room temperature. MOZ‐ON is utilized for the preparation of MOZ‐amino acids under various conditions. The oxime can be recovered and reused. The combination of Cl‐Z‐ and MOZ‐ for the alternative masking of the N 4 ‐ and N 4 ‐amino groups of lysine residue has also been studied.