129982-29-2Relevant articles and documents
Asymmetric Synthesis of β-Amino Acid Derivatives by Michael Addition to Chiral 2-Aminomethylacrylates
Barnish, Ian T.,Corless, Martin,Dunn, Peter J.,Ellis, David,Finn, Paul W.,et al.
, p. 1323 - 1326 (1993)
The addition of lithium enolates to chiral aminomethylacrylates 7 and 8 proceeded with excellent diastereodifferentiation (up to 98percent de) and provided an expeditious synthesis of homochiral β-aminomethylglutarates 9 and 10, on a scale of up to 500g.T
The chemical development and scale-up of sampatrilat
Dunn, Peter J.,Hughes, Michael L.,Searle, Patricia M.,Wood, Albert S.
, p. 244 - 253 (2013/09/06)
The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.
