Cyclic carbamate analogs of pilocarpine

P Sauerberg, J Chen, E WoldeMussie…

Index: Sauerberg, Per; Chen, June; WoldeMussie, Elizabeth; Rapoport, Henry Journal of Medicinal Chemistry, 1989 , vol. 32, # 6 p. 1322 - 1326

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Citation Number: 31

Abstract

A number of pilocarpine analogues containing the (S)-3-ethyl-4-[(4'-imidazolyl) methyl]-2- oxazolidinone (9) structural feature were synthesized from L-histidine. With 1-benzyl-L- histidine as the key intermediate, a regiospecific synthetic route was developed to the N"- methyl derivative 8. The regiochemistry of the alkylation of the imidazole nucleus was determined by measuring proton cross-ring coupling constants in the high-field'H NMR. ...