cas 1179522-58-7, (2R,4S)-3-(tert-butoxycarbonyl)-2-tert-butyl-4-methyloxazolidine-4-carboxylic acid

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Synthesis of cytimidine through a one-pot copper-mediated amidation cascade
A concise synthesis of cytimidine was developed utilizing tandem Cu-mediated N-aryl amidations followed by global deprotection. This sequence exploits a regioselective coupling of an iodobenzamide with a halopyrimidine that allows the union of three fragments in a single synthetic manipulation and will permit the efficient and rapid diversification of the cytimidine core.
Serrano, Catherine M.,Looper, Ryan E.
supporting information; experimental part
p. 5000 - 5003
(2011/11/13)

Complementary syntheses of N,O-protected-(S)-2-methylserine on a multikilogram scale
Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with >99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic l-serine derivative under cryogenic conditions. The four-step telescoped process, starting from l-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3- oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.
Anson, Michael S.,Clark, Hugh F.,Evans, Paul,Fox, Martin E.,Graham, Jonathan P.,Griffiths, Natalie N.,Meek, Graham,Ramsden, James A.,Roberts, Alastair J.,Simmonds, Shaun,Walker, Matthew D.,Willets, Matthew
experimental part
p. 389 - 397
(2012/02/02)