Mycophenolic acid derivative, preparation method thereof and application thereof
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Embodiment 1
[0098] Example 1 (E)-6-(1,3-dihydro-4-hydroxyl-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl- Preparation of 4-Hexenol
[0099] (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl-4- Hexenoic acid (3.2g, 10mmol, purchased from Changzhou Huaren Chemical Co., Ltd.) was dissolved in tetrahydrofuran (50mL), triethylamine (2.8mL) was added, the mixed solution was cooled to -10°C, and ethyl chloroformate was added dropwise Solution (prepared by dissolving 1.958mL of ethyl chloroformate in 5mL of tetrahydrofuran), stirred and reacted at -10°C for 1h, then filtered the reaction solution, and the filtrate was dropped into an aqueous sodium borohydride solution cooled by an ice-water bath (from 2.3g Sodium borohydride was dissolved in 20mL of water), slowly returned to room temperature after dropping, stirred and reacted for 5h, then stopped stirring, slowly poured the reaction solution into hydrochloric acid (1mol / L, 100mL), stirred evenly and used Extr...
Embodiment 2
[0101] Example 2 (E)-6-(1,3-dihydro-4-hydroxyl-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl- Preparation of methyl 4-hexenoate
[0102] (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl-4- Hexenoic acid (3.2g, 10mmol) and p-toluenesulfonic acid (138mg, 0.801mmol) were dissolved in methanol (80mL), stirred and reacted at room temperature for 6h, during which a large amount of white solid precipitated, after the reaction, distilled methanol After drying, the obtained solid was washed several times with water, and dried to obtain 3.079 g (yield: 92%) of the title compound having the following structure.
[0103] 1 H-NMR (300MHz, CDCl 3 , δppm): 7.67(s, 1H), 5.24(t, J=6.6Hz, 1H), 5.20(s, 2H), 3.76(s, 3H), 3.62(s, 3H), 3.38(d, J= 6.9Hz, 2H), 2.40(td, J=2.1Hz, 8.1Hz, 2H), 2.30(t, J=8.1Hz, 2H), 2.15(s, 3H), 1.80(s, 3H)
[0104]
Embodiment 3
[0105] Example 3 (E)-6-(1,3-dihydro-4-hydroxyl-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl- Preparation of ethyl 4-hexenoate
[0106] (E)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxobenzofuran-5-yl)-4-methyl-4- Hexenoic acid (1.0g, 3.122mmol) was dissolved in ethanol (50mL), 3 drops of concentrated sulfuric acid was added, and the reaction was stirred at room temperature for 6h. After the reaction, the ethanol was evaporated to dryness, and the obtained solid was washed several times with water, and dried to obtain 3.079g (Yield: 92%) The title compound having the following structure.
[0107] 1 H-NMR (300MHz, CDCl 3 , δppm): 7.07(s, 1H), 5.24(td, J=1.8Hz, 6.6Hz, 1H), 5.20(s, 2H), 4.07(q, J=6.9Hz, 2H), 3.76(s, 3H ), 3.38(d, J=6.6Hz, 2H), 2.39(td, J=2.4Hz, 7.8Hz, 2H), 2.30(t, J=7.8Hz, 2H), 2.15(s, 3H), 1.80( s, 3H)
[0108]
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