Chemoselective N-deprotection of tert-butyl 2-(trifluoroacetylamino) esters under PTC conditions: Synthesis of tert-butyl 2-aminocarboxylates

被引：7
|
作者：
Albanese, D
Corcella, F
Landini, D
Maia, A
Penso, M
机构：
[1] UNIV MILAN,CTR CNR,I-20133 MILAN,ITALY
[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 03期
关键词：
D O I：
10.1039/a604902h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Trifluoroacetamide 1 is alkylated in good yields (77-83%) by tert-butyl 2-bromocarboxylates 3 under solid-liquid phase transfer catalysis (PTC) conditions [anhydrous K2CO3, triethyl(benzyl)ammonium chloride (TEBA; 10%), MeCN, 80 degrees C], The resulting tert-butyl 2-(trifluoroacetylamino) carboxylates 5 are chemoselectively hydrolysed in 75-95% yields to the corresponding tert-butyl 2-amino carboxylates, isolated as hydrochlorides 8, under liquid-liquid PTC conditions [CH2Cl2 or Et(2)O, aqueous 20% KOH, TEBA (10%), 25-40 degrees C].
引用
收藏
页码：247 / 249
页数：3
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