Macrocyclic picolinamides as fungicides
A technology of fungi and heterocyclic groups, applied in the direction of fungicides, biocides, biocides, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0113] Example 1, Step 1: Preparation of (3R, 4R, 5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one:
[0114]
[0115] With rapid stirring, the N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxane -3-yl)-3-hydroxy-4-methoxypyridine-2-amide (prepared as described in Ricks, Michael J. et al. in US 6,706,7402004) (20.0 grams (g), 38.7 mmol ( mmol), 1.00 equivalent) in 6M HCl (200 milliliters (mL)) was heated to 100 ℃. After 1 hour (h), the resulting brown solution was cooled to 23 ℃ and used ether (Et 2 O; 2x 200mL) extraction. Combine the organic extracts and use saturated sodium bicarbonate (NaHCO 3 ) Aqueous solution (100mL) washed with magnesium sulfate (MgSO 4 ) Dry, filter and concentrate to obtain (3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one (5.62g, 70%), yellowish brown solid.
[0116] Example 1, Step 2: Preparation of (3R, 4R, 5S)-3-benzyl-5-methyl-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one :
[0117]
[0118] At 0℃ (ice water bath), ad...
Embodiment 2
[0131] Example 2, Step 1: N-[(3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-triisopropylsilyloxy-1,5 -Dioxinan-3-yl]-N-tert-butoxycarbonyl carbamate (Compound 55):
[0132]
[0133] To ((3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxo-8-((triisopropylsilyl)oxy)-1,5-dioxa Cyclononan-3-yl) tert-butyl carbamate (5.00g, 9.33mmol, 1.00 equivalent) in anhydrous CH 3 DMAP (0.570 g, 4.67 mmol, 0.500 equivalents) and di-tert-butyl dicarbonate (4.07 g, 18.7 mmol, 2.00 equivalents) were added to the solution in CN (93 ml) and the resulting solution was stirred at room temperature overnight. The orange solution was concentrated and purified directly by automated silica gel column chromatography (1-10% acetone / hexane) to obtain N-[(3S,7S,8R,9S)-7-benzyl-9-methyl-2-oxy Subo-8-triisopropylsilyloxy-1,5-dioxanonane-3-yl]-N-tert-butoxycarbonyl carbamate (5.78g, 97%), Viscous, colorless oily substance: IR (ATR) 2942, 2867, 1743, 1707, 1603, 1495, 1456, 1357, 1313.1252, 1206, 1172, 1146, 1121, 1088, 1064, 1014, 945...
Embodiment 3
[0149] Example 3, Step 1: N-[(3S,7S,8R,9S)-7-benzyl-8-methoxy-9-methyl-2-oxo-1,5-dioxane Alk-3-yl]-N-tert-butoxycarbonyl carbamate (Compound 74)
[0150]
[0151] At 0℃ (ice water bath), to N-[(3S,7S,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2-oxo-1,5-dioxane Alk-3-yl)-N-tert-butoxycarbonyl carbamate (250mg, 0.521mmol, 1.00 equivalent) in CH 2 Cl 2 (5.2mL, 0.1M) was added proton sponge (335mg, 1.56mmol, 3.00 equivalent) and trimethyloxonium tetrafluoroborate (116mg, 0.782mmol, 1.50 equivalent) into the solution. The resulting white suspension was stirred at 0°C for 30 minutes (min), removed from the cold bath and stirred at room temperature for 5 hours, then poured into 1 / 2 saturated NaHCO 3 Solution (20 mL). Use CH 2 Cl 2 (3x 20mL) The mixture was extracted, and the combined organic phase was washed with 1N HCl (20mL) and washed with Na 2 SO 4 Dry, filter and concentrate to give an oil. Purified by automated silica gel column chromatography to obtain N-[(3S,7S,8R,9S)-7-benzyl-8-metho...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More