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With triethylamine; In dichloromethane; at 20℃; for 2h; |
Example 11; Preparation of Cp 9360; A solution of 70.5 grams of <strong>[148043-73-6]4,4,5,5,5-pentafluoropentane-1-ol</strong> in 1330 grams of dichloromethane was cooled under nitrogen and diluted with 59 grams of triethylamine followed by 54.5 grams of methanesulfonyl chloride. The solution was kept at 20 C. for 2 hours and then diluted with 1000 grams of water and agitated overnight. Evaporation of the organic phase afforded 109 grams of Cp 9360. |
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With triethylamine; In hexane; dichloromethane; water; |
(Step 8) 1-Methylsulfonyloxy-4,4,5,5,5-pentafluoropentane <strong>[148043-73-6]4,4,5,5,5-pentafluoropentan-1-ol</strong> (25 g, 0.13 mol) was dissolved in dichloromethane (50 ml) and cooled to 0 C., and then triethylamine (46 ml, 0.33 mol) and methylsulfonylchloride (20.4 ml, 0.26 mol) were added thereto. The reaction mixture was stirred for 3 hours at room temperature. After the reaction was completed, water was added to the reaction solution and the resulting mixture was extracted with dichloromethane. The organic layer was washed with 1M hydrochloric acid solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The product was purified by silica gel column chromatography (eluent: 50% ethyl acetate in n-hexane) to give the title compound (34 g, Yield: quantitative) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3) delta: 4.30(t, 2H), 3.05(s, 3H), 2.30~2.05(m, 4H) |
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With triethylamine; In dichloromethane; |
(Step 1) 4,4,5,5,5-Pentafluoropentyl Iodide 4,4,5,5,5-Pentafluoropentan-1-ol (100 g, 0.56 mol) and triethylamine (200 ml) were added to dichloromethane (2,000 ml) under argon atmosphere and cooled to 0 C. Methylsulfonylchloride (52 ml, 0.67 mol) was slowly added dropwise thereto and stirred for 1.5 hour. Ice which had been broken into pieces was added to stop the reaction, and the organic layer was washed with water and saturated saline solution and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=4/1, v/v) to give 1-methylsulfonyloxy-4,4,5,5,5-pentafluoropentane (160 g, quantitative) as a yellow oil. |
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In dichloromethane; water; |
Example 1 Synthesis of 1-iodo-4,4,5,5,5-pentafluoropentane Trietylamine (46 ml, 0.330 mol) was added to a solution of <strong>[148043-73-6]4,4,5,5,5-pentafluoropentan-1-ol</strong> (25 g, 0.132 mol) in dichloromethane (50 ml). To this solution, methanesulfonyl chloride (20.4 ml, 0.264 mol) was added at 0 C., followed by stirring for 3 hours at room temperature under argon atmosphere. After the reaction was completed, water was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was washed with 1N aqueous hydrochloric acid, water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=1/1) to give 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (34 g, quantitative). 1H-NMR (300 MHz, CDCl3): d 4.30 (t, 2H), 3.05 (s, 3H), 2.30-2.05 (m, 4H). |
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With triethylamine; In dichloromethane; at 20℃; for 0.5h; |
To a solution of 100mu?(0.416mmol) of <strong>[148043-73-6]4,4,5,5,5-pentafluoropentan-1-ol</strong> in 2 mL of dichloromethane were added 69mu? (1.2 eq) of triethylamine and 36mu? (1.1 eq) of methanesulfonyl chloride in the order, followed by stirring at room temperature for 30 min. The solution was washed with an aqueous saturated sodium bicarbonate solution, dried over sodium sulfate, filtrated and concentrated to produce a colorless oil. 60mu? of the oil, 30 mg of (R)-tert-butyl (2-(3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-5-(piperazin-1-yl)-2,3-dihydropyrimidin-1(6H)-yl)-1-phenylethyl)carbamate (0.049mmol), and 21 mg (0.149 mmol) of potassium carbonate were dissolved at 80C for 7 hrs in 2 mL of acetonitrile, with stirring. The solution was concentrated, diluted with dichloromethane, and washed with an aqueous saturated sodium bicarbonate solution. After concentration of the organic layer thus formed, the residue was purified by prep-TLC (eluent: hexane/ethyl acetate, 1/1) and dried in a vacuum to afford 8 mg of the compound as a colorless oil (yield 21%). 1H NMR (300MHz, CDCl3) delta 1.36 (9H, s), 1.77 (2H, m), 2.14 (4H, m), 2.36 (3H, s), 2.42 (2H, m), 2.53 (2H, m), 2.75 (2H, m), 3.61 (2H, m), 4.05 (1H, m), 4.28 (1H, m), 5.01 (1H, m), 5.33(1H, m), 5.51 (1H, m), 5.82 (1H, d), 7.19-7.44 (7H, m), 7.55 (1H, m) |
| 27 g |
With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; |
20 g of pentafluoropentanol and 21 ml of triethylamine are dissolved in 400 ml of methylene chloride at ambient temperature under inert atmosphere. [0081] The mixture is cooled to 0/5C, 9.7 ml of mesyl chloride are added followed by agitation in a cold bath for about 2 hours. [0082] At the end of the reaction, monitored by TLC with 7/3 toluene/ ethyl acetate, 100 ml of water are added and the mixture extracted with 200 ml of methylene chloride. The solvent is evaporated under reduced pressure to obtain 27 g of <strong>[148043-73-6]4,4,5,5,5-pentafluoropentanol</strong> mesylate as an oily product, which is used as such. |
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With triethylamine; In acetonitrile; at 20℃; for 4h;Inert atmosphere; |
Synthesis of compound 17 A 250 ml flask containing a solution of compound 18 (20 g, 1 12.3 mmol) in 50 ml of dry acetonitrile under inert nitrogen atmosphere. Triethylamine (19.9 ml, 142.6 mmol) and a solution of Methanesulfonyl chloride (9.9 ml, 128 mmol) in 35 ml ACN were slowly added at a temperature below 20 C. The mixture was stirred at room temperature 4 h. The mixture was concentrated by evaporating most of the ACN and extracted with CH2CI2. The organic phase was washed with saturated NaCI solution, dried over anhydrous MgS04, filtered and evaporated to dryness. 24.45 g of a yellow liquid was obtained (122% by mass). |
| 14.14 g |
With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling with ice; |
,4,5,5,5-pentafluoropentanol (10 g) and dichloromethane (100 mL) were added to the reaction flask, Triethylamine (11.3 g) was added and the mixture was added dropwise under ice-cooling Methylsulfonyl chloride (6.72 g) was added dropwise and the reaction was resumed at room temperature for 2 hours. Excess triethylamine and methylsulfonyl chloride were washed with water, dried over anhydrous sodium sulfate and spin dried to give 14.14 g <strong>[148043-73-6]4,4,5,5,5-pentafluoropentanol</strong> methanesulfonate. |
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With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling with ice; |
<strong>[148043-73-6]4,4,5,5,5-pentafluoropentanol</strong> (10 g) and methylene chloride (100 ml) is added to the reaction flask. Add triethylamine (11.3 g). Under ice bath, drop methanesulfonyl chloride (6.72 g). The completion of the dropping. Restoration to room temperature react for 2 hours. Water to wash the excess triethylamine and methyl chloride, dried with anhydrous sodium sulfate, turns on lathe does, get 14.14 g 4,4,5,5,5-pentafluoropentyl methanesulfonate. |
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