3-diethoxyphosphorylpropanoic acid

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Use as a reaction vessel a 500 milliliter (mL) single neck round bottomed flask fitted with a condenser with a nitrogen inlet. Charge the vessel with 3-(diethyoxyphosphoryl)propanoic acid (20.30 g) followed by the addition of water (150 mL) and aluminum hydroxide monohydrate (2.709 g). Heat the resulting solution to 90° C. and hold at that temperature for eight hours. Remove the water using a rotovap to leave behind a solid material. Add 100 mL of acetone and isolate the solid by vacuum filtration using a Buchner funnel and wash with acetone (100 mL). Transfer the solid product to a glass bottle and place in a vacuum oven to dry overnight. The yield of the solid product, aluminum tris(3-(diethoxyphosphoryl)propanoate), is 12.45 g. Use as a reaction vessel a 500 milliliter (mL) single neck round bottomed flask fitted with a condenser with a nitrogen inlet Remove the water using a rotovap to leave behind a solid material isolate the solid by vacuum filtration wash with acetone (100 mL) to dry overnight

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 40.3 mmol of benzyl 3-diethylphosphonopropionate (12.1 g) are dissolved in 100 ml of ethanol, and 2 g of catalyst (5% Pd/C) are added. After stirring under an H2 atmosphere for 4 h, the active carbon is filtered off, and the solvent is distilled out. The product results as a colourless oil which slowly solidifies to a colourless solid at room temperature. The product is slightly contaminated with ethyl 3-diethylphosphono-propionate which, where appropriate, can be transferred into the organic phase by shaking several times with water and hexane, and be removed. the active carbon is filtered off the solvent is distilled out The product results as a colourless oil which slowly solidifies to a colourless solid at room temperature be removed

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 3-(diethylphosphono)propanoic acid (79, 1.0 g, 4.76 mmol) in H2O (12 mL) and CH2Cl2 (12 mL) was added NaHCO3 (1.0 g, 11.9 mmol) and TBAHSO4 (1.62 g, 4.76 mmol). After stirring for 20 min, S-ethyl O-iodomethyl carbonothioate (1.17 g, 4.76 mmol) in CH2Cl2 (2 mL) was added. The biphasic reaction was stirred vigorously for 4 h 20 min and was diluted with water and CH2Cl2. The layers were separated, the organic layer was washed with H2O, 0.5 N HCl solution, saturated NaHCO3 solution, saturated NaCl solution, dried over MgSO4, filtered and concentrated to dryness. The crude product was triturated with Et2O and the solids were removed by filtration and rinsed with small portions of Et2O. After concentration, the combined filtrates were purified by flash chromatography on a Biotage™ flash chromatography system, using EtOAc as the eluent, to yield compound 80 (1.29 g, 83%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.30-1.65 (m, 9H), 2.03-2.12 (m, 2H), 2.64-2.71 (m, 2H), 2.90 (q, J=7.4 Hz, 2H), 4.06-4.14 (m, 4H), 5.82 (s, 2H). 31P NMR (162 MHz, CDCl3) δ 30.45 (s). The biphasic reaction was stirred vigorously for 4 h 20 min The layers were separated the organic layer was washed with H2O, 0.5 N HCl solution, saturated NaHCO3 solution, saturated NaCl solution dried over MgSO4 filtered concentrated to dryness The crude product was triturated with Et2O the solids were removed by filtration rinsed with small portions of Et2O After concentration the combined filtrates were purified by flash chromatography on a Biotage™ flash chromatography system

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Use as a reaction vessel a 500 milliliter (mL) single neck round bottomed flask fitted with a condenser with a nitrogen inlet. Charge the vessel with 3-(diethyoxyphosphoryl)propanoic acid (20.30 g) followed by the addition of water (150 mL) and aluminum hydroxide monohydrate (2.709 g). Heat the resulting solution to 90° C. and hold at that temperature for eight hours. Remove the water using a rotovap to leave behind a solid material. Add 100 mL of acetone and isolate the solid by vacuum filtration using a Buchner funnel and wash with acetone (100 mL). Transfer the solid product to a glass bottle and place in a vacuum oven to dry overnight. The yield of the solid product, aluminum tris(3-(diethoxyphosphoryl)propanoate), is 12.45 g. Use as a reaction vessel a 500 milliliter (mL) single neck round bottomed flask fitted with a condenser with a nitrogen inlet Remove the water using a rotovap to leave behind a solid material isolate the solid by vacuum filtration wash with acetone (100 mL) to dry overnight