Inova 400 400mhz spectrometer

All compounds and reagents were purchased from Sigma-Aldrich, Acros, Alfa Aesar, Combi-blocks, and EMD Millipore unless otherwise noted and were used without further purification. Thin layer chromatography with Merck silica plates (60-F254), using UV light as the visualizing agent, was used to monitor reaction progress. Flash column chromatography was carried out using a Teledyne Isco Combiflash Nextgen 300+ machine using Luknova SuperSep columns (SiO₂,25 μm) with ethyl acetate and hexanes as eluents. ¹H NMR spectra were recorded on a Varian INOVA-400 400MHz spectrometer. Chemical shifts are reported in δ units (ppm) relative to residual solvent peak. Coupling constants (J) are reported in hertz (Hz). Characterization data are reported as follows: chemical shift, multiplicity (s=singlet, d=doublet, t=triplet, q=quartet, br=broad, m=multiplet), coupling constants, number of protons, mass to charge ratio. The compound’s identity was confirmed via high-resolution mass spectrometry.

General procedures: Reactions were monitored either by TLC and/or analytic HPLC (UV, detection, 220 nm). Flash columns, filled with silica gel Merck 60 (230–400) were used for chromatographic separations. A reversed-phase column, Sunfire C18 (4.6 × 50 mm, 3.5 µm), a flux of 1 mL/min, and mixtures of CH₃CN, phase A, and H₂O, phase B, both containing 0.01% formic acid, were used for analytical HPLCs. Mass spectra, in electrospray, positive mode, were obtained on a Waters Micromass ZQ spectrometer. High resolution mass spectrum (ESI-HRMS) was recorded on an Agilent 6520 Q-TOF instrument. Optical rotation for final compound RGM8-51 was measured in a polarimeter Perkin Elmer 141 apparatus. NMR spectra were recorded in a Varian INOVA-400 (400 MHz) spectrometer, operating at 400 and 100 MHz for ¹H and ¹³C experiments, respectively (with chemical shifts expressed in ppm and coupling constants in Hz).

The ¹⁹F-NMR spectra were recorded on a Varian Inova-400 (400 MHz) Spectrometer with dichloromethane as solvent. All chemical shifts are quoted on the δ-scale in units of parts per million (ppm), relative to hexafluorobenzene and using residual protonated solvent as the internal standard.