6642-21-3Relevant academic research and scientific papers
Studies Related to Thietan-2-ones. Part 1. Conversion of D-Penicillamine into DL-2-Methylpenicillamine using Thietan-2-one-based Chemistry
Al-Zaidi, Shakir M.R.,Crilley, Martine M. L.,Stoodley, Richard J.
, p. 2259 - 2266 (2007/10/02)
A series of N-substituted derivatives of (3R)-3-amino-4,4-dimethylthietan-2-one has been prepared from D-penicillamine (3).Attempts to effect the methylathion at position 3 of the N-acetyl (7a), N,N-diacetyl (12), N-benzyloxycarbonyl (7b), or N-(p-nitrobenzylidene) derivative (15a) were unrewarding.Although the N-benzylidene and N-furfurylidene derivatives (15b) and (15c) were successfully methylated at position 3 by using iodomethane and potassium t-butoxide in tetrahydrofuran (THF), best results were achieved by treating the N-(2-hydroxy-1-naphthylmethylene) derivative (15d) with iodomethane and sodium hydride in N,N-dimethylformamide.Cleavage of the imine linkage of the methylated derivatives of the thietanones (15c) and (15d), i.e. compounds (19b) and (19c), was effected by using, respectively, toluene-p-sulphonic acid in THF and dilute hydrochloric acid in acetone.The derived salts of (3RS)-3-amino-3,4,4-trimethylthietan-2-one, i.e. (21a) and (21b), underwent hydrolysis in boiling water to give the corresponding salts of DL-2-methylpenicillamine, i.e. (22a) and (22b).
