0.5 mmol of 2-hydroxy substituted aromatic aldehyde, 0.75 mmol (45 mg) of urea and 0.08 mmol (30 mg) of Cu(OTf)2 were added to a microwave vial with a magnetic stirrer and dissolved in 1 ml of DMSO. Subsequently, 0.46 mmol (50 μl) of methyl acetoacetate was added to a vial, which was sealed and irradiated at 100 °C in a microwave reactor for 2 h at a maximum power of 200 W (CEM Discover™ System). At the end of reaction time, the reaction mixture was poured on ice; the precipitate was formed, filtered, washed with distilled water and dried. Further purification of compounds was done by the Biotage Isolera One Flash Chromatography System (cyclohexane–ethyl acetate–methanol).![]()
Isolera one flash chromatography system
Manufactured by Biotage
The Isolera One Flash Chromatography System is a laboratory instrument designed for automated flash chromatography. It is capable of performing sample purification and compound isolation using a pre-packed flash chromatography column.
Automatically generated - may contain errors
5 protocols using isolera one flash chromatography system
1
Copper-Catalyzed Knoevenagel Condensation
2
Glycine-Based Peptide Synthesis
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Fmoc-glycine-OH (342
mg, 1.2 mmol) or Boc-glycine-OH (210
mg, 1.2 mmol) was dissolved in CH2Cl2 (0.05
M solution) at 0 °C under magnetic stirring. EDC (202 mg, 1.3
mmol) and HOBt (176 mg, 1.3 mmol) were added, and the solution was
stirred for 1 h at 0 °C. Then, compound3 (1 equiv)
was added and the pH was corrected to 7–8 with DIPEA (364 μL).
The reaction was stirred at 25 °C overnight. The mixture was
washed with a solution of KHSO4 (5% w/v), then with a saturated
solution of NaHCO3 (20 mL) and finally with a saturated
solution of NaCl (20 mL). The organic layer was dried over anhydrous
Na2SO4, filtered, and evaporated under reduced
pressure. Pure products4a –f were
purified by a Biotage Isolera One Flash Chromatography System affording
white solids.
mg, 1.2 mmol) or Boc-glycine-OH (210
mg, 1.2 mmol) was dissolved in CH2Cl2 (0.05
M solution) at 0 °C under magnetic stirring. EDC (202 mg, 1.3
mmol) and HOBt (176 mg, 1.3 mmol) were added, and the solution was
stirred for 1 h at 0 °C. Then, compound
was added and the pH was corrected to 7–8 with DIPEA (364 μL).
The reaction was stirred at 25 °C overnight. The mixture was
washed with a solution of KHSO4 (5% w/v), then with a saturated
solution of NaHCO3 (20 mL) and finally with a saturated
solution of NaCl (20 mL). The organic layer was dried over anhydrous
Na2SO4, filtered, and evaporated under reduced
pressure. Pure products
purified by a Biotage Isolera One Flash Chromatography System affording
white solids.
3
Synthesis of Organic Compounds Using Standard Techniques
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All manipulations and reactions were performed using standard Schlenk techniques. The starting materials, reagents, and solvents were obtained from commercial suppliers and were used without further purification. Thin-layer chromatography was performed with Merk silica gel 60 F254 pre-coated glass sheets. Column chromatography was performed on Biotage Isolera One™ flash chromatography system and the eluting solvents are noted as a mixed solvent with given volume-to-volume ratios or as a percentage. Uncorrected melting points were measured using Optimelt Automated Melting Point System (Stanford Research Systems). 1H and 13C NMR were measured on a 400 MHz Bruker Avance or a 500 MHz Agilent 500 NMR spectrometer. Chemical shifts and coupling constants are presented in parts per million (ppm) relative to Me4Si and hertz (Hz), respectively, and the following abbreviations are used: s, singlet; d, doublet; dd, a doublet of doublets; t, triplet; m, multiplet. High-resolution mass spectra were performed on Waters ACQUITY UPLC BEH C18 1.7µ−Q-TOF SYNAPT G2-Si High Definition Mass Spectrometry.
4
Synthesis of Fmoc-alanine Conjugates
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Fmoc-alanine-OH (218 mg, 0.7 mmol) was dissolved in CH2Cl2 (0.05 M solution) at 0 °C under magnetic
stirring. DIC (88.3 mg, 110 μL, 0.7 mmol) and OXIMA (156 mg,
1.1 mmol) were added to the solution, and the stirring was continued
for 1 h at 0 °C. Then, compound3a (201 mg, 0.7
mmol) was added and the pH was corrected with DIPEA (215 μL).
The reaction was monitored by TLC (AcOEt/hexane, 1:1). The mixture
was stirred at 25 °C overnight. The solution was washed with
a solution of KHSO4 (5% w/v), then with a saturated solution
of NaHCO3 (20 mL) and a saturated solution of NaCl (52
mL). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. Pure diastereoisomers4 g/4′g were separated by a Biotage Isolera
One Flash Chromatography System (from hexane 100% to hexane/AcOEt
50:50) as white solids.
stirring. DIC (88.3 mg, 110 μL, 0.7 mmol) and OXIMA (156 mg,
1.1 mmol) were added to the solution, and the stirring was continued
for 1 h at 0 °C. Then, compound
mmol) was added and the pH was corrected with DIPEA (215 μL).
The reaction was monitored by TLC (AcOEt/hexane, 1:1). The mixture
was stirred at 25 °C overnight. The solution was washed with
a solution of KHSO4 (5% w/v), then with a saturated solution
of NaHCO3 (20 mL) and a saturated solution of NaCl (52
mL). The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. Pure diastereoisomers
One Flash Chromatography System (from hexane 100% to hexane/AcOEt
50:50) as white solids.
5
Chromatographic Purification and Spectroscopic Analysis of Trioxsalen
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Trioxsalen (CAS Number: 3902‐71‐4) was purchased from TCI. Thin‐layer chromatography (TLC) was done on silica gel 60 Å F254 aluminium sheets (Merck). Synthesized compounds were purified using the preparative flash column chromatography (Isolera One flash chromatography system, Biotage) which was carried out on silica gel, 60 Å (Fluka). Solvents for TLC, column chromatography, and extractions were commercial grade. NMR spectra were recorded on a Bruker Av400 at a resonance frequency of 400 MHz (for 1H NMR), 101 MHz (for 13C NMR) or 162 MHz (for 31P NMR). Solvent signals were used as internal standards. Chemical shifts (δ) are given in ppm. 1H NMR spectra are described as follows: multiplicity, the coupling constant J [Hz], the number of protons (integral). Multiplicity in the 1H NMR spectra is described as s=singlet, d=doublet, dd=doublet of doublets, dt=doublet of triplets, ddd=doublet of doublet of doublets, t=triplet and m=multiplet. For 13C and 31P NMR spectra, only the chemical shifts of signals are given. High‐resolution mass spectrometry (HR‐MS) was performed by the MS service of the Laboratory for Organic Chemistry at the ETH Zürich. The ESI‐HR‐MS spectra were recorded on a Bruker Daltonics maXis (ESI‐QTOF‐MS).
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