37418-88-5, 4-Hydroxyisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Example 16 5-(4-Methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid; To a solution of 4-hydroxy-isobenzofuran-1,3-dione (195 mg, 1.2 mmol) in anhydrous N,N-dimethylformamide (4 ml) under nitrogen was added minutes and then methyl iodide (0.37 ml, 6.0 mmol) was added. The reaction was stirred for 48 h. and then quenched with saturated ammonium chloride. The mixture was concentrated in vacuo, diluted in ethyl acetate (20 ml) and the organic phase washed with 1N hydrochloric acid (5 ml) and brine (3.x.5 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. To the crude solid was added methanol causing a precipitate to form. The flask was cooled in an ice bath for 2 h. and the solid filtered off, washed with methanol and dried in vacuo which afforded 0.1 g (47percent) of 4-methoxy-isobenzofuran-1,3-dione as a solid.1H NMR (300 MHz, DMSO-d6) delta 7.95 (t, J=8, 1H), 7.61 (d, J=8, 1H), 7.58 (d, J=8, 1H), 3.99 (s, 3H).APCI-MS: [M+H]+=179.1A solution of 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (122 mg, 0.43 mmol, prepared as described in Example 17) and 4-methoxy-isobenzofuran-1,3-dione (92 mg, 0.52 mmol) was prepared in distilled tetrahydrofuran (4 ml) under nitrogen. 1-hydroxybenzotriazole (87 mg, 0.65 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (123 mg, 0.65 mmol), and triethylamine (0.29 ml, 2.15 mmol) were added. The reaction was stirred at ambient temperature for 18 h., then concentrated in vacuo. The crude mixture was diluted with ethyl acetate (25 ml) and washed with 1N hydrochloric acid (5 ml), saturated sodium bicarbonate (5 ml), and brine (5 ml). The organic layer was dried (Na2SO4), filtered, and the solvent evaporated in vacuo to give 0.18 g (94percent) of 2-amino-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester.1H NMR (300 MHz, CDCl3) delta 7.66 (t, J=7, 1H), 7.43 (d, J=7, 1H), 7.19 (d, J=7, 1H), 4.59-4.46 (m, 2H), 4.06-3.72 (m, 3H), 4.00 (s, 3H), 2.87-2.81 (m, 1H), 2.60-2.51 (m, 1H), 1.48 (s, 9H).To a solution of the above 2-amino-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.18 g, 0.42 mmol) in distilled dichloromethane (5 ml) under nitrogen was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (0.25 g, 1.26 mmol) and triethylamine (0.23 ml, 1.68 mmol). The reaction was stirred for 12 h., concentrated in vacuo and reconstituted in ethyl acetate (25 ml). The organic layer was washed with 1N hydrochloric acid (2.x.5 ml), saturated sodium bicarbonate (5 ml), and brine (5 ml). The resulting solution was dried (Na2SO4), filtered, and the solvent evaporated in vacuo. The crude material was purified by silica gel chromatography using a gradient of ethyl acetate/dichloromethane (0 to 10percent gradient). Pure fractions were collected and the solvent evaporated in vacuo to give 195 mg (81percent) of 2-(tert-butoxyoxalyl-amino)-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as an oil.1H NMR (300 MHz, CDCl3) delta 12.48 (s, 1H), 7.65 (t, J=7, 1H), 7.43 (d, J=7, 1H), 7.19 (d, J=7, 1H), 4.77 (d, J=15, 1H), 4.63 (d, J=15, 1H), 4.04-3.75 (m, 3H), 4.00 (s, 3H), 2.94 (d, J=17, 1H), 2.65 (dd, J=17, 10, 1H), 1.58 (s, 9H), 1.53 (s, 9H).LC-MS: Rt=4.17 min, [M+H]+=573.2The above 2-(tert-butoxyoxalyl-amino)-5-(4-methoxy-1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.15 g, 0.26 mmol) was dissolved in a mixture of 50percent trifluoroacetic acid/dichloromethane (5 ml). The reaction was stirred at ambient temperature for 7 h., concentrated in vacuo and the residue evaporated in vacuo from dichloromethane (3.x.10 ml). The resulting precipitate was washed with dichloromethane and dried in vacuo to give 100 mg (83percent) of the title compound as a solid.1H NMR (300 MHz, DMSO-d6) delta 12.31 (s, 1H), 7.79 (t, J=8, 1H), 7.48 (d, J=8, 1H), 7.42 (d, J=8, 1H), 4.74 (d, J=15, 1H), 4.56 (d, J=15, 1H), 3.95 (s, 3H), 3.91-3.79 (m, 2H), 3.69-3.63 (m, 1H), 2.98 (d, J=17, 1H), 2.57 (dd, J=17, 10, 1H).LC-MS: Rt=1.26 min, [M+H]+=461.0HPLC (254.4 nm): Rt=3.10 min, 100percent
37418-88-5, 37418-88-5 4-Hydroxyisobenzofuran-1,3-dione 96580, abenzofuran compound, is more and more widely used in various fields.
Reference£º
Patent; Novo Nordisk A/S; US7115624; (2006); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem