A practical synthesis of 2,2-difluoro-3-amino-propanoic acid (α,α-difluoro-β-alanine)

被引:14
作者
Cheguillaume, A [1 ]
Lacroix, S [1 ]
Marchand-Brynaert, J [1 ]
机构
[1] Univ Catholique Louvain, Unite Chim Organ & Med, B-1348 Louvain, Belgium
关键词
difluoro-beta-alanine; benzotriazolyl-l-methylamine; Reformatsky reaction;
D O I
10.1016/S0040-4039(03)00243-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reformatsky reaction of ethyl bromodifluoroacetate with N,N-(dibenzyl)-1H-benzotriazolyl-1-methylamine gave fully protected alpha,alpha-difluoro-beta-alanine. Hydrogenolysis and hydrolysis furnished alpha,alpha-difluoro-beta-alanine. Further transformation into N-phthalimido-alpha,alpha-difluoro-beta-alanine was described. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2375 / 2377
页数:3
相关论文
共 19 条
[1]  
Aguilar N, 1998, SYNTHESIS-STUTTGART, P313
[2]   [18F]-EF5, a marker for PET detection of hypoxia:: synthesis of precursor and a new fluorination procedure [J].
Dolbier, WR ;
Li, AR ;
Koch, CJ ;
Shiue, CY ;
Kachur, AV .
APPLIED RADIATION AND ISOTOPES, 2001, 54 (01) :73-80
[3]   Synthesis of S-thioacyl dithiophosphates, efficient and chemoselective thioacylating agents [J].
Doszczak, L ;
Rachon, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (10) :1271-1279
[4]  
Filler R., 1993, ORGANOFLUORINE COMPO
[5]   The Mitsunobu reaction in the synthesis of α,α-difluoro-β-amino acids [J].
Fokina, NA ;
Kornilov, AM ;
Kukhar, VP .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 111 (01) :69-76
[6]  
JORGENSEN AS, 2000, Patent No. 0240446
[7]   Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia [J].
Josse, O ;
Labar, D ;
Georges, B ;
Grégoire, V ;
Marchand-Brynaert, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :665-675
[8]  
Josse O, 1999, SYNTHESIS-STUTTGART, P404
[9]   THE CHEMISTRY OF N-SUBSTITUTED BENZOTRIAZOLES .14. NOVEL ROUTES TO SECONDARY AND TERTIARY-AMINES AND TO N,N-DISUBSTITUTED HYDROXYLAMINES [J].
KATRITZKY, AR ;
YANNAKOPOULOU, K ;
LUE, P ;
RASALA, D ;
UROGDI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02) :225-233
[10]   Benzotriazole mediated syntheses of α-fluoro-β-amino esters [J].
Katritzky, AR ;
Nichols, DA ;
Qi, M .
TETRAHEDRON LETTERS, 1998, 39 (39) :7063-7066