A Convenient Synthesis of (E)-4-Alkoxy-2-amino-3-butenoic Acid Derivatives

Autor:	Kazuhiro Kobayashi, Miyuki Tanmatsu, Osamu Morikawa, Taichi Kitamura, Susumu Irisawa, Hisatoshi Konishi, Hideki Akamatsu, Masaki Takahashi
Rok vydání:	1999
Předmět:	Hexamethylphosphoric Triamide chemistry.chemical_classification Hydrolysis chemistry.chemical_compound Chemistry 3-butenoic acid Alkoxy group Substituent Organic chemistry Halide General Chemistry Alkylation Alkyl
Zdroj:	Bulletin of the Chemical Society of Japan. 72:2307-2313
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.72.2307
Popis:	(E)-4-Alkoxy-2-formylamino-3-butenoic acid esters have been prepared in two steps from 3-alkoxy-1-isocyanopropenes. The method is based on the reaction of 3-alkoxy-1-isocyano-1-lithiopropenes, which can be generated by the treatment of 3-alkoxy-1-isocyanopropenes with LDA in THF at −78 °C, with alkyl chlorocarbonates, affording 4-alkoxy-2-isocyano-3-butenoates. These isocyano esters have been easily transformed into the corresponding formylamino esters by treating with concd HCl in Et2O at −20 °C. Subsequently, the introduction of a substituent into the 2-position has been achieved by ethoxycarbonylation with ethyl chlorocarbonate, followed by alkylation with alkyl halides by using hexamethylphosphoric triamide (HMPA) as a co-solvent. The resulting alkylated isocyano 3-butenoates have been similarly hydrolyzed with concd HCl to the corresponding 2-formylamino-3-butenoates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c43d7ad48ac6d829508316a8e5a9640d https://doi.org/10.1246/bcsj.72.2307 Zobrazit plný text záznamu