Apex 4 ftms instrument

The reactions were carried out in oven-dried glassware. All reactions were carried out under anhydrous conditions with freshly distilled solvents under a positive pressure of argon unless otherwise noted. Umemoto’s reagent refers to S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate. The reactions were monitored using thin-layer chromatography (TLC) on silica-gel-coated aluminum plates (60 F₂₅₄, E. Merck). Column chromatography was performed on silica gel (200–300 mesh). Gel filtration was performed on Sephadex LH-20 (Pharmacia). Optical rotations were obtained on a Hanon P850 Automatic Polarimeter. Experiments under ultraviolet (UV) irradiation were carried out using a safe and stable mercury lamp spotlight system purchased from Beijing Zhongjiao Jinyuan Technology Co., Ltd. (Item No. CEL-M500). ¹H NMR spectra were recorded at room temperature for solutions in CDCl₃ or D₂O with Avance III-400 or III-600 instruments (Bruker), and the chemical shifts were referenced to the peak for TMS (0 ppm, CDCl₃) or external CH₃OH (3.34 ppm, D₂O). ¹³C NMR spectra were recorded using the same NMR spectrometers, and the chemical shifts were reported relative to the internal CDCl₃ (δ = 77.16 ppm) or external CH₃OH (49.70 ppm, D₂O). High-resolution mass spectrometry (HRMS) experiments were performed on a Waters Xevo G2 Q-TOF spectrometer or a Bruker APEX IV FTMS instrument.

Ibuprofen and naproxen were obtained from National Institute for Food and Drug Control. All liquid reagents were distilled before use. The other chemicals and reagents were obtained from commercial sources.
The melting point was measured on a YRT-3 melting point apparatus (Shantou Keyi Instrument & Equipment Co. Ltd., Shantou, China). Infrared (IR) spectra were obtained on a Perkin Elmer983 (Perkin Elmer, Norwalk, CT). ¹H-NMR spectra were taken on a Varian INOVA 400 (Varian, Palo Alto, CA) using CDCl₃, dimethylsulfoxide-d6 (DMSO-d₆) and D₂O as solvent. High-resolution mass spectroscopy data of the product were collected on a Waters Micromass GCT or a Bruker Apex IV FTMS instrument. Reversed-phase chromatography performed on C18 chromatographic analysis was carried out using the high-performance liquid chromatography (HPLC) system (Shimadzu, Kyoto, Japan) consisted of a RF-530 fluorescence detector (Shimadzu) and Allchorom plus data operator, respectively. A Diamonsil column (200 × 4.6 mm, 5 mm) was used. A LC-10A liquid chromatographic system (Shimadzu) and a reverse-phase HPLC column (ODS-C18 column, 4.6 × 200 mm, 5 mm, SinoChrom, Dalian, P.R. China) were used.

In order to monitor the chemistry synthesis reaction, the analytical thin-layer chromatography (TLC) was conducted on the pre-coated plates (silica gel GF254).and the resulted spots were visualized with UV light. Melting points (mp) were determined on a X-4 microscopic melting point apparatus (Yu Hua, China) and were uncorrected. All synthesized title compounds were identified by high resolution mass spectrometry (HRMS) analyses on a Bruker Apex IV FTMS instrument (Bruker Company, Boston, MA, USA). The 1 H NMR spectra was recorded at 400 MHz on a Bruker AM-400 spectrometer (Bruker Company, Boston, MA, USA) in DMSO-d6 or CDCl₃. Chemical shifts (δ) were expressed in part per million (ppm) with TMS as an internal standard.