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DL‐homoserinehydroxamic Acid, DL‐homo‐cystinedihydroxamic Acid, and Derivatives by Hydroxylaminolysis of γ‐Hydroxy‐ and γ‐Thio‐Lactones
Author(s) -
Knobler Y.,
Bittner S.,
Frankel M.
Publication year - 1970
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197000076
Subject(s) - chemistry , aminolysis , hydroxylamine , thio , hydroxamic acid , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The reaction of α‐amino‐, α‐carbamoylamino‐, α‐benzamido‐, and α‐benzyloxycarbonyl‐amino‐γ‐butyrolactone with hydroxylamine led to the formation of DL‐homoserinehydroxamic acid and α‐N‐acyl derivatives. α‐N‐Benzoyl‐DL‐homoserine‐N‐methyl‐hydroxamic acid and O‐benzylhydroxamic acid ester were prepared by reacting α‐benzamido‐γ‐butyrolactone with N‐methylhydroxylamine and with O‐benzylhydroxylamine, respectively. Hydroxyl‐aminolysis of DL‐homocysteinethiolactone and of N‐acyl‐DL‐homocysteinethiolactones gave homocystinedihydroxamic acid and N,N′‐disubstituted derivatives. Relative reactivities of O‐ and S‐lactones were compared.