37924-85-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3-(Bromomethyl)benzo[d]isoxazole, cas is 37924-85-9,the Benzisoxazole compound, it is a common compound, a new synthetic route is introduced below.
Step 1: To a -78 C solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[bl[1,4ldiazepin- 3-yl)-carbamic acid tert-butyl ester (807 mg, 2.91 mmol) in THF (19.4 mL) was added lithium bis(trimethylsilyl)amide (3.2 mL, 1.0 M solution in THF, 3.2 mmol), dropwise. The mixture was stirred at -78 C for 15 mm, then a mixture of Nal (523 mg, 3.49 mmol) and 3- (bromomethyl)benzo[dlisoxazole (740 mg, 3.49 mmol) in THF (9.7 mL) was added dropwise over 10 mm. The mixture was stirred at -78 C for 50 mm., warmed to RT and stirred for 4.5 h. The mixture was diluted with 1 N citric acid and extracted with EtOAc. The combined extractswere washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide a -4:1 mixture of (S)-tert-butyl 1-(benzo[dlisoxazol-3-ylmethyl)-2- oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1 ,4jdiazepin-3-ylcarbamate and (S)-tert-butyl 1- (benzo [djisoxazol-3 -ylmethyl)-4-oxo-2,3 ,4,5 -tetrahydro- 1 H-benzo [bI [1,41 diazepin-3-ylcarbamate (742 mg, 63 %) as a yellow foam. LC-MS mlz 431 [M+Naj.Step 1: To a 0C solution of -4:1 mixture of tert-butyl (S)-1-((S)-1-(benzo[djisoxazol-3- ylmethyl)-2-oxo-2,3 ,4,5-tetrahydro- 1 H-benzo [bI [1,41 diazepin-3 -ylamino)- 1 -oxopropan-2- yl(methyl)carbamate and tert-butyl (S)-i -((S)-i -(benzo[dlisoxazol-3-ylmethyl)-4-oxo-2,3 ,4,5- tetrahydro- 1 H-benzo [bI [1 ,4ldiazepin-3-ylamino)- 1 -oxopropan-2-yl(methyl)carbamate (209.4 mg, 424 tmol) in CH2C12 (4.24 mL) was added pyridine (343 tL, 4.24 mmol), followed by methyl 4-(chlorocarbonyl)benzoate (92.7 mg, 467 tmol). After 1 h at 0 C the mixture was diluted with H20 and extracted with CH2C12. The combined extracts were washed with 1 N aq. citric acid, sat. aq. NaHCO3, and brine, dried over Na2504, filtered, and concentrated. The residue was purified by flash chromatography. The resulting material was repurified by flash chromatography to provide methyl 4-((S)-5-(benzo[djisoxazol-3 -ylmethyl)-3 -((S)-2-(tert-butoxycarbonyl(methyl)amino) propanamido)-4-oxo-2,3 ,4,5 -tetrahydro- 1 Hbenzo[b l[1,4ldiazepine-1-carbonyl)benzoate (194 mg, 70 %) as a white solid. LC-MS mlz 678 [M+Naj .
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3-(Bromomethyl)benzo[d]isoxazole, 37924-85-9
Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Shaoqing; DONNELL, Andrew F.; KESTER, Robert Francis; LE, Kang; LOU, Yan; MICHOUD, Christophe; REMISZEWSKI, Stacy; RUPERT, Kenneth C.; WEISEL, Martin; WO2015/71393; (2015); A1;,
Benzisoxazole – Wikipedia
Benzisoxazole – an overview | ScienceDirect Topics