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CAS No. : | 20931-50-4 | MDL No. : | MFCD21604057 |
Formula : | C9H18O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 158.24 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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99% | With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20℃; for 8h; | To a solution of <strong>[1197-66-6]2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one</strong> (prepared according to PCT Int. AppL, WO2010021680) (2.30 g, 14.72 mmol) in 14 mL of THF and 5 mL of ethano was added sodium borohydri.de (0.56 g, 14.72 mmol) and the mixture stirred at RT for 8 hrs. The mixture was diluted with 50 mL of EtOAc and washed with 50 mL of 0.2 N HC1 and 50 mL of brine. The aqueous layer was again extracted with EtOAc (3 x 50 mL) and the organic fractions combined, dried over sodium sulfate and concentrated to give 2.30 g (99%) of compound lc as a white solid that was used without further purification. NMR ( CHLOROFORM-d) delta: 4.13 fit, J - 11.4, 4.3 Hz, 1H), 1.94 (dd, J = 12.5, 4.2 Hz, 2), 1.28 f s, 6H), 1.27 - 1.22 (m, 8H). |
With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 1h; | A. 2,2,6,6-Tetramethyl-tetrahydro-2H-pyran-4-ol, 10a (0297) (0298) A solution of <strong>[1197-66-6]2,2,6,6-tetramethyloxan-4-one</strong> (190 mg, 1.22 mmol) and NaBH4 (93 mg, 2.5 mmol) in THF (4 mL) and methanol (2 mL) was stirred for 1 h at RT. The reaction was then quenched by the addition of 0.1 mL of water. The resulting mixture was concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether (1:5-1:3 v/v)) to give the compound 10a. 1H-NMR (300 MHz, CDCl3) delta (ppm): 3.88-3.97 (m, 1H), 1.71-1.77 (m, 2H), 1.36-1.37 (m, 1H), 1.20-1.25 (m, 1H), 0.97-1.05 (m, 6H), 0.89-0.95 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
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Example 269 2-(2-Chlorophenyl)-N-{3-sulfamoyl-4-[(2,2,6,6-tetramethyltetrahydro-2H-pyran-4- yl)oxy]phenyl}acetamide 2,2,6,6-Tetramethyltetrahydro-2H-pyran-4-ol (251 mg, 1.59 mmol) was dissolved in dimethylformamide (10 mL) and treated with sodium hydride (296 mg, 7.40 mmol, purity 60%). After 10 min <strong>[96-72-0]2-chloro-5-nitrobenzenesulfonamide</strong> (250 mg, 1.06 mmol) was added and it was stirred overnight at room temperature. It was quenched at 0 C with water and the solvent was removed in vacuo. Water and dichloromethane were added, it was extracted with dichloromethane, the organic phases were combined, washed with brine and dried over sodium sulfate prior to being concentrated in vacuo yielding crude 5-nitro- 2-[(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)oxy]benzenesulfonamide (286 mg). The crude material from the previous step was dissolved in methanol (3 mL), flushed with nitrogen and treated with Pd/C (30 mg, 0.28 mmol) under a hydrogen atmosphere (1 bar). After stirring for 6 hours at room temperature the catalyst was filtered off, it was washed with methanol followed by concentration in vacuo yielding crude 5-amino-2-[(2,2,6,6- tetramethyltetrahydro-2H-pyran-4-yl)oxy]benzenesulfonamide (126 mg). The crude material from the previous step was dissolved in dimethylformamide (3 mL) and treated with (2-chlorophenyl)acetic acid (71.4 mg, 0,42 mmol), N,N-diisopropylethylamine (148mg, 1.14 mmol) and HATU (159 mg, 0.42 mmol). The reaction mixture was stirred overnight at room temperature, then it was concentrated in vacuo. Ethyl acetate and water were added, the organic phase was dried and concentrated in vacuo. Purification by preparative HPLC (Chromatorex C-18 10mum, 125x30mm, acetonitrile/water + 0.1% aqueous ammonia (32%)) led to 2-(2-chlorophenyl)-N-{3-sulfamoyl-4-[(2,2,6,6- tetramethyltetrahydro-2H-pyran-4-yl)oxy]phenyl}acetamide (25 mg, 0.0520 mmol, 3 % yield over 3 steps, 98 % purity). LC-MS (Method B): Rt = 1.17 min MS (ESIneg): m/z = 479 (M-H)+ 1H-NMR (400MHz, DMSO-d6) [ppm]: 1.16 (s, 6H), 1.29 (s, 6H), 1.52 (t, 2H), 2.01 (dd, 2H), 3.81 (s, 2H), 4.93 - 5.04 (m, 1H), 6.85 (s, 2H), 7.24 - 7.35 (m, 3H), 7.38 - 7.48 (m, 2H), 7.76 (dd, 1H), 8.03 (d, 1H), 10.32 (s, 1H). |