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A practical synthesis of 2,2-difluoro-3-amino-propanoic acid (alpha,alpha-difluoro-beta-alanine)

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Cheguillaume, A Lacroix, Simon [UCL] Marchand-Brynaert, Jacqueline [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2003
Language Anglais
Journal information "Tetrahedron Letters" - Vol. 44, no. 11, p. 2375-2377 (2003)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4039
e-issn 1873-3581
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords difluoro-beta-alanine ; benzotriazolyl-l-methylamine ; Reformatsky reaction
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Bibliographic reference Cheguillaume, A ; Lacroix, Simon ; Marchand-Brynaert, Jacqueline. A practical synthesis of 2,2-difluoro-3-amino-propanoic acid (alpha,alpha-difluoro-beta-alanine). In: Tetrahedron Letters, Vol. 44, no. 11, p. 2375-2377 (2003)
Permanent URL http://hdl.handle.net/2078.1/41165