Supporting InformationGeneral. Microanalyses were performed by Galbraith Laboratories or Atlantic Microlab. The actual charges of substrates and reagents are given below. The molar amounts are calculated based on the assays of the materials. Similarly, yields are calculated based on assay corrected moles of substrates and products. Proton ( 1 H) nuclear magnetic resonance (NMR) spectra were recorded on either a Unity Inova Varian 300 MHz or Unity Inova Varian 400 MHz spectrometer. 1 H NMR descriptions are reported as: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet) or br (broad).Carbon ( 13 C) nuclear magnetic resonance (NMR) spectra were recorded on either a Unity Inova Varian 300 or Unity Inova Varian 400 spectrometer at 75 MHz and 100 MHz, respectively.Melting points were determined using a Laboratory Devises Mel-Temp Instrument equipped with a Fluke 51 Thermocouple. Thin-layer chromatography was performed on EM Science 0.25 nm Silica Gel 60, glass-backed plates with F 254 indicator. UV light was employed for visualization. Flash chromatography was performed on Universal Scientific 0-63 mesh Silica Gel. Liquid chromatography and mass spectrum analysis were performed on an Agilent 1100 Series LC/MSD model number G1946D equipped with an APCI ionization source and photodiiode array. Chiral HPLC method for separation of
Studies directed toward the process research, development, and scale-up preparation of the potential r v β 3 integrin antagonist 1 are described. A convergent approach is detailed wherein tetrahydropyrimidine hydroxybenzoic acid 2 is linked to the β-amino acid ester 3 via a diisoproylcarbodiimide, catalytic HOBt coupling reaction. Saponification of the resulting ethyl ester, isolation of the corresponding zwitterion, H 3 PO 4 salt formation, crystallization, and acetonitrile-to-acetone exchange give rise to 1 as a crystalline monohydrate in 67% overall yield from 4.
AnEfficient Asymmetric Synthesis of (3S)-3-Amino-1-(4cyanophenyl)-2-oxopyrrolidine Hydrochloride Salt.-Coupling of bromide (II) with nitrile (III) and subsequent cyclization gives the lactam ring of the title compound. Displacement of the bromide in intermediate (IV) by treatment with excess NH 4 OH and work-up of the racemic amine with (R)-mandelic acid (V) leads to isolation of the racemic (R)-mandelic acid salt (VI). The optically pure title compound is then obtained through the dynamic resolution of amine (VI) in the presence of a catalytic amount of salicyl aldehyde and (R)-mandelic acid. -(COLSON, P.-J.; PRZYBYLA, C. A.; WISE, B. E.; BABIAK, K. A.; SEANEY, L. M.; KORTE, D. E.; Tetrahedron: Asymmetry 9 (1998) 15, 2587-2593; Monsato Life Sci., Searle, Synth. Dev., Skokie, IL 60077, USA; EN)
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