219310-11-9Relevant articles and documents
Enantioselective, chromatography-free synthesis of β3-Amino acids with natural and unnatural side chains
Gerfaud, Thibaud,Chiang, Ying-Ling,Kreituss, Imants,Russak, Justin A.,Bode, Jeffrey W.
experimental part, p. 687 - 696 (2012/07/13)
β3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstrated with the preparative scale synthesis of two valuable β3-amino acids possessing unnatural side chains.
New access to racemic β3-amino acids
Nejman, Micha?,?liwińska, Anna,Zwierzak, Andrzej
, p. 8536 - 8541 (2007/10/03)
A general simple procedure having the potential for large scale preparations of racemic β3-amino acids has been developed. The procedure involves base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran. Hydrolysis of the adducts by refluxing with 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent purity.
Intermediates of peripherally selective N-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists
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, (2008/06/13)
Intermediates of N-carbonyl-3,4,4-substituted piperidines are provided which are useful in the preparation of peripheral opioid antagonists.
β-Aminopenicillins, salts and esters
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, (2008/06/13)
β-Aminopenicillins, Salts and Esters are described having a wide spectrum of activity against Gram-positive and Gram-negative organisms. The β-aminopenicillins are derivatives of 6-amino-penicillanic acid and the procedure for preparing the β-aminopenicillins is set forth. β-aminopenicillins are characterized by having in the 6-position side chain a cycloalkyl ring of 5 - 7 carbon atoms particularly cyclopentyl, cyclohexyl or cycloheptyl.