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Hydrazide as a Carboxyl Protecting Group deprotection by acidolysis
Author(s) -
Schnyder Jörg,
Rottenberg Max
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580222
Subject(s) - chemistry , hydrazide , perchloric acid , acetic acid , bromide , yield (engineering) , hydrogen bromide , phenylalanine , glycine , organic chemistry , protecting group , medicinal chemistry , amino acid , biochemistry , materials science , alkyl , metallurgy , bromine
Elimination of the hydrazide group was studied with the model compounds N‐benzoyl‐glycine hydrazide and N‐benzoyl‐ L ‐phenylalanine hydrazide, using phosphorus oxychloride, hydrogen bromide or hydrogen chloride in acetic acid, or 60% perchloric acid. It was found that treatment of N‐benzoyl‐ L ‐phenylalanine hydrazide with perchloric acid gave N‐benzoyl‐ L ‐phenylalanine in 100% yield and without racemisation.