The synthetic route of 3663-80-7 has been constantly updated, and we look forward to future research findings.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3663-80-7,2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid,as a common compound, the synthetic route is as follows.
To a stirred solution of l,4-benzodioxane-2-carboxylic acid (9.0 g, 50 mmol), HATU (19.0 g, 50 mmol) and DIPEA (35 mL) in DMF (100 mL) was added (R)-1-phenylethanamine (6.4 mL, 50 mmol) at 22 ¡ãC, and the mixture was allowed to stir at 22 ¡ãC for 16 hrs. Water (200 mL) was added, and the mixture was stirred at 22¡ãC for 10 hrs. The aqueous layer was decanted, and the sticky residue was washed with water carefully, dried, and purified by flash chromatography to give (R)-N-((R)-l-phenylethyl)-2,3-dihydrobenzo [bj [1 ,4j dioxine-2-carboxamide (2) 5.3 g (37 percent) and (S)-N-((R)- 1 -phenylethyl)-2,3 – dihydrobenzo[bj[1,4jdioxine-2-carboxamide (3) 5.7 g (40 percent). 2: ?H NMR (500 MHz, CDC13) 7.40?7.26 (m, 5H), 6.96 ? 6.84 (m, 4H), 6.79 (d, J= 7.2 Hz, 1H), 5.22?5.10 (m, 1H), 4.64 (dd, J= 7.5, 2.6 Hz, 1H), 4.56 (dd, J= 11.4, 2.6 Hz, 1H), 4.17 (dd, J= 11.4, 7.6 Hz, 1H), 1.47 (d, J= 6.9 Hz, 3H). ?3C NMR (125 MHz, CDC13) 166.1, 143.3, 142.4, 141.6, 128.8, 127.6, 126.2, 122.4, 121.9, 117.6, 117.1, 73.1, 65.5, 48.6, 21.7. APCI-MS mlz: 284 (M+H)t 3: ?H NMR (500 MHz, CDC13) 7.38 ? 7.27 (m, 3H), 7.26 ? 7.21 (m, 2H), 7.05 ?7.00 (m, 1H), 6.99 ? 6.92 (m, 3H), 6.85 (d, J = 6.7 Hz, 1H), 5.29 ? 5.20 (m, 1H), 4.77 (dd, J =7.3, 2.6 Hz, 1H), 4.59 (dd, J= 11.4, 2.7 Hz, 1H), 4.22 (dd, J= 11.4, 7.3 Hz, 1H), 1.61 (d, J= 6.9Hz, 3H). ?3C NMR (125 MHz, CDC13) 166.2, 143.3, 142.5, 141.5, 128.7, 127.4, 125.8, 122.5,121.9, 117.7, 117.1, 73.2, 65.4, 48.4, 21.9. APCI-MS mlz: 284 (M+H)t
The synthetic route of 3663-80-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; NORTHWESTERN UNIVERSITY; KRAINC, Dimitri; SILVERMAN, Richard, B.; ZHENG, Jianbin; (84 pag.)WO2019/27765; (2019); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem