171049-14-2Relevant articles and documents
A practical and robust process to produce SB-214857, Lotrafiban, ((2S)-7-(4,4′-bipiperidinylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3- oxo-1H-1, 4-benzodiazepine-2-acetic acid) utilising an enzymic resolution as the final step
Walsgrove, Timothy C.,Powell, Lawson,Wells, Andy
, p. 488 - 491 (2002)
During the scale-up of a chemical process to produce phase II supplies of the chiral compound Lotrafiban, partial racemisation occurred to produce drug substance of unacceptable chiral purity. A new route capable of producing several hundred kilograms of Lotrafiban of high chiral purity had to be rapidly identified and scaled up. The strategy adopted was to employ an enzymic resolution as the final step, thus introducing the chirality under very mild conditions to prevent any racemisation. This was achieved using an immobilised form of the Candida antarctica B lipase in water at 30°C. The biotransformation was demonstrated to be a robust, reliable, and an economic way to introduce the chirality into the Lotrafiban molecule.
Polymer-supported catalase: A green approach to the removal of hydrogen peroxide from reaction mixtures
Alston, Mark,Willetts, Andy,Wells, Andy
, p. 505 - 508 (2002)
During a programme of work directed at developing a manufacturing route for SB 214857, Lotrafiban, the need arose to find methodology for efficiently destroying hydrogen peroxide in aqueous solutions of the penultimate intermediate, SB 270051. Whilst this was initially achieved using a chemical process, a biotransformation process has now been developed that utilises a polymer-supported catalase enzyme to remove peroxide from reaction mixtures. The biocatalytic approach provides an economic and environmentally friendly solution to peroxide removal when compared to the chemical process.
CuI-catalyzed coupling reaction of beta-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction. Facile synthesis of SB-214857.
Ma,Xia
, p. 2583 - 2586 (2007/10/03)
[reaction: see text] The CuI-catalyzed coupling reaction of aryl halides with beta-amino acids or beta-amino esters is completed at 100 degrees C in 48 h, which indicates that the structure of the beta-amino acid has an accelerating effect for the Ullmann
