Convenient Preparation of tert-Butyl β-(Protected amino)esters

Refluxing an aldehyde 1 with benzotriazole and benzylcarbamate in the presence of a catalytic amount of p-TsOH gave the corresponding benzyloxycarbonylamino-1-(1-benzotriazolyl)alkane 2 in good yields. Compounds 2 treated with substituted tert-butyl acetates 3 using LDA as a base afford smoothly and...

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Veröffentlicht in:Journal of organic chemistry 2002-07, Vol.67 (14), p.4957-4959
Hauptverfasser: Katritzky, Alan R, Kirichenko, Kostyantyn, Elsayed, Ahamad M, Ji, Yu, Fang, Yunfeng, Steel, Peter J
Format: Artikel
Sprache:eng
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Zusammenfassung:Refluxing an aldehyde 1 with benzotriazole and benzylcarbamate in the presence of a catalytic amount of p-TsOH gave the corresponding benzyloxycarbonylamino-1-(1-benzotriazolyl)alkane 2 in good yields. Compounds 2 treated with substituted tert-butyl acetates 3 using LDA as a base afford smoothly and under mild conditions the N-2-protected 3-aminoalkanoic esters 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0110810