Chiralcel od h

Manufactured by Daicel

Sourced in Japan

Chiralcel OD-H is a chiral stationary phase used for high-performance liquid chromatography (HPLC) analysis. It is composed of polysaccharide-based cellulose derivatized with 3,5-dimethylphenylcarbamate. The Chiralcel OD-H column is designed to separate enantiomers of chiral compounds.

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Lab products found in correlation

Chiralpak ad h, by Daicel (2 mentions) Chemstation software, by Agilent Technologies (1 mentions) Agilent 1200 system, by Agilent Technologies (1 mentions) Silica gel 60n, by Kanto Chemical (1 mentions) Ecx 400, by JEOL (1 mentions) Ecs 400, by JEOL (1 mentions) Jms 700tz mass spectrometer, by JEOL (1 mentions) Sepa 300 digital polarimeter, by Horiba (1 mentions) Fs hydrodex β 6tbdm, by Macherey-Nagel (1 mentions) Gc fid 2010, by Shimadzu (1 mentions) Fluostar omega fluorimeter, by BMG Labtech (1 mentions) Ltq ion trap mass spectrometer, by Thermo Fisher Scientific (1 mentions) Micromass q tof micro synapt high definition mass spectrometer, by Waters Corporation (1 mentions) Axs smart apex 2 single crystal x ray diffractometer, by Bruker (1 mentions) Chiralpak ic column, by Daicel (1 mentions)

7 protocols using chiralcel od h

Purification and Characterization of Enantiomerically Pure Pyridyl-Benzothiazole Piperidine Derivative

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Example 241

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N-(6-amino-5-methyl-3-pyridyl)-2-[(5S)-5-methyl-2-[2-(3-pyridyl)-1,3-benzothiazol-5-yl]-1-piperidyl]-2-oxo-acetamide (50 mg, 0.103 mmol) was purified by SFC (Instrument: Berger, Multigr AM-II; Column: Daicel Chiralcel OD-H 250 mm×30 mm×5 m; Mobile phase: supercritical CO₂/EtOH (0.1% NH₃—H₂O, v %)=55/45; Flow Rate: 80 mL/min; Column Temperature: 38° C.; Nozzle Pressure: 100 bar; Nozzle Temperature: 60° C.; Evaporator Temperature: 20° C.; Trimmer Temperature: 25° C.; Wavelength: 220 nm) to afford N-(6-amino-5-methyl-3-pyridyl)-2-[(2R,5S)-5-methyl-2-[2-(3-pyridyl)-1,3-benzothiazol-5-yl]-1-piperidyl]-2-oxo-acetamide (44.4 mg, single known enantiomer with trans relative chemistry, peak 2, retention time: 8.370 min, white solid). ¹H NMR (400 MHz, methanol-d₄) δ ppm 9.27 (br s, 1H), 8.70 (br s, 1H), 8.26-8.57 (m, 2H), 7.99-8.23 (m, 2H), 7.39-7.88 (m, 3H), 5.49-5.89 (m, 1H), 3.77-4.13 (m, 1H), 3.50 (br s, 1H), 2.37 (br s, 2H), 2.25 (br s, 2H), 2.13 (br s, 1H), 1.85-2.09 (m, 2H), 1.50 (br s, 1H), 1.15 (br d, J=6.5 Hz, 3H); LCMS (ESI) [M+H]⁺ m/z: calcd 487.2, found 487.3; HPLC: 100%@254 nm; 100% ee, 99.5% de.

US11492350B2. Compounds and methods of use (2022-11-08). Tango Therapeutics, Inc. [US]. Inventors: Kevin M. Cottrell [US], John P. Maxwell [US].

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Enantioselective HPLC Separation of Sulfoxide Compounds

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Compounds 1–4 were separated on a Jasco HPLC system consisting of a PU-2089 pump, an AS-2055 sampler, a CO-2060 column thermostat, a MD-2010 detector and a CD-2095 detector. All the chiral columns including Chiralpak AD-H, AS-H, Chiralcel OD-H, and OJ-H (Daicel Chemical Industries, Tokyo, Japan) were 250 × 4.6 mm i.d. with a 5 µm particle size. The detection wavelength of 1–4 was set at 275, 275, 240, and 285 nm, respectively. The chromatographic parameters for the enantioselectivity evaluation of the CSPs including retention factor (k), separation factor (α), and resolution factor (Rs) for the enantiomers were calculated.
The samples dissolved in EtOH: n-Hex (80:20, v/v) were formulated as the solution of 2 mg/mL for analysis and 5 mg/mL for preparation. The enantiopure isomers of 1–4 were prepared under the optimal separation condition of our study, on Chiralpak AD-H, Chiralcel OD-H, Chiralpak AS-H and AD-H columns, respectively. Also, the high enantiomeric purities (enantiomeric excesses >99%) of the isolated sulfoxide enantiomers were verified by the enantioselective HPLC system.

Xiong F., Yang B.B., Zhang J, & Li L. (2018). Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs. Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry, 23(10), 2680.

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HPLC Analysis of Chiral Compounds

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The HPLC analyses were performed using an Agilent 1200 system (Agilent, Santa Clara, CA, USA) equipped with a quaternary pump (G1311A), column thermostat (G1316A), degasser unit (G1322A), autosampler (G1329A), and diode-array detector (G1315D). A Chiralcel OD-H (250 mm × 4.6 μm, 5 μm; Daicel, Japan) column was used for separation. The mobile phase was an n-hexane–ethanol mixture (20:80, v/v) at a flow rate of 0.7 mL∙min⁻¹. Acetic acid (0.2% in ethanol (v/v)) and triethylamine (0.2% in ethanol (v/v)) were used as additives. The detection wavelength was 294 nm, 20 μL of analyte was injected, and the column temperature was 25 °C [29 (link)]. The HPLC system was controlled and the data were analyzed using a computer equipped with ChemStation software (Rev.B.04.02, Agilent).

Wang Y.F., Jin H.X., Wang Y.G., Yang L.Y., OuYang X.K, & Wu W.J. (2016). Synthesis and Characterization of Magnetic Molecularly Imprinted Polymer for the Enrichment of Ofloxacin Enantiomers in Fish Samples. Molecules, 21(7), 915.

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NMR Spectroscopy and HPLC Analysis Protocol

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1 H-NMR spectra were recorded on a JEOL ECX-400 (400 MHz) or JEOL ECS-400 (400 MHz) in CDCl 3 with tetramethylsilane (δ = 0.00) as internal standard. Chemical shifts are reported in part per million (ppm), and signal are expressed as singlet (s), doublet (d) , triplet (t), quartet (q), multiplet (m), and broad (br). 13 C-NMR spectra were recorded on a JEOL ECX-400 (100MHz) in CDCl 3 (δ = 77.00) with tetramethylsilane as an internal standard (δ = 0.0). Chemical shifts are reported in part per million (ppm). HPLC analysis was directly performed with chiral stationary phase column, Chiralpak AD-H or Chiralcel OD-H purchased from DAICEL Co., Ltd. High resolution mass spectra (HRMS) were recorded on a JEOL JMS 700TZ mass spectrometer at the Center for Instrumental Analysis, Hokkaido University. Optical rotations were measured on a HORIBA SEPA-300 digital polarimeter. Kanto Chemical silica gel 60N (particle size 0.063-0.210 mm) was used for flash column chromatography. RuCl and RuCl 2 (nbd)(MeCN) 2 17 were prepared by the literature procedure. BIPAM ligand (Me-BIPAM) were prepared according to our previous procedure. 18 Me-BIPAM was commercially available from Wako Pure Chemical Industries, Ltd. Phthalide was purchased from commercial source and substituted phthalides were synthesized according to known literature. 19

Yohda M, & Yamamoto Y. (2015). Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones. Organic & biomolecular chemistry, 13(44).

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Chiral Analysis of Arylmalonic Acids

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All chemicals were purchased from Sigma-Aldrich (Steinheim, Germany). Arylmalonic acids 3b, 3c and 3d were kindly provided by Chiracon GmbH (Teltow, Germany). Fluorescence and absorption were measured with a FLUOstar Omega Fluorimeter (BMG Labtech GmbH Ortenberg, Germany) DNA samples were sequenced by the DNA sequencing service of the department of biochemistry at Ruhr-University Bochum. Kits for ligation, DNA isolation and restriction were purchased at Fermentas (St. Leon-Rot, Germany). Enzyme affinity purification was done using a 1 mL His Pure Ni-NTA column (Pierce Biotechnology Rockford, USA). Chiral GC analyses were carried out using the chiral column FS-Hydrodex-β-6TBDM [heptakis-(2,3-di-O-methyl-6-O-t-butyldimethylsilyl)-β-cyclodextrin] (Macherey Nagel, Germany) on a GC-FID-2010 (Shimadzu, Japan). Retention times for 2b (160°C) were 31.5 min (S) and 32.3 min (R) for 2c (170°C) 12.9 min (S) and 14.4 min (R). The elution order was identified using commercial (S)-naproxen (TCI Chemicals, Japan). Chiral HPLC analyses were carried out using the column CHIRALCEL OD-H (Daicel, Osaka, Japan) on a L-7110 HPLC device (Hitachi High Tech, Tokyo, Japan) using n-hexane/i-propanol/trifluor acetic acid (98:2:0.5). With a flow rate of 0.5 mL, the two enantiomers of phenyl methyl malonic acid ethyl ester 2a eluted with 55 min (S) and 65 min (R).

Bartsch M., Gassmeyer S.K., Köninger K., Igarashi K., Liauw P., Dyczmons-Nowaczyk N., Miyamoto K., Nowaczyk M.M, & Kourist R. (2015). Photosynthetic production of enantioselective biocatalysts. Microbial Cell Factories, 14, 53.

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Enantiomeric Separation of Reticuline

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Separation of the (R)- and (S)- enantiomers of reticuline was performed using the chiral column CHIRALCEL OD-H (4.6x250mm, Daicel Chemical Industries) and the solvent system hexane:2-propanol:diethylamine (78:22:0.01) at a flow rate of 0.55 ml min^-1 [18 (link)]. Following LC separation, metabolites were injected into an LTQ ion trap mass spectrometer (Thermo Electron, San Jose, CA) and detected by selected reaction monitoring (SRM). SRM transitions of m/z 288→164.0 (CID@35) and 330→192 (CID@30) were used to detect reticuline. Retention times for reticuline obtained in samples matched retention times observed with authentic standards.

Fossati E., Narcross L., Ekins A., Falgueyret J.P, & Martin V.J. (2015). Synthesis of Morphinan Alkaloids in Saccharomyces cerevisiae. PLoS ONE, 10(4), e0124459.

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Chiral NMR and X-ray Analysis Protocol

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¹H NMR (400 MHz), ¹³C NMR (100 MHz) and ¹⁹F NMR (376 MHz) spectra were recorded on Brucker Asend 400 spectrometers. HRMS was performed on Waters Micromass Q-TOF micro Synapt High Definition Mass Spectrometer. HPLC analysis using a chiral stationary phase was performed on Shimadzu or Dalian Elite (UV230+ UV/Vis Detector and P230P High Pressure Pump). CHIRALCEL OD-H or CHIRALPAK IC column was purchased from Daicel Chemical Industries, Ltd. Single-crystal X-ray diffraction data were recorded on Bruker-AXS SMART APEX II single-crystal X-ray diffractometer. See Supplementary Figs 1–62 for the NMR spectra and HPLC chromatograms, Supplementary Table 1 for the optimization of reaction, Supplementary Discussion for the mechanism studies and computational details and Supplementary Methods for the characterization data of compounds not listed in this part.

Zhang D., Zhou J., Xia F., Kang Z, & Hu W. (2015). Bond cleavage, fragment modification and reassembly in enantioselective three-component reactions. Nature Communications, 6, 5801.

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