Hydrazide as a Carboxyl Protecting Group deprotection by acidolysis | Zendy

Schnyder Jörg | Zendy; Rottenberg Max | Zendy

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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.

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