Reference of 5961-59-1, A common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of 62 (tert-butoxycarbonyl)-l-phenylalanine (1, 8.75mmol, 2.3g) in 15mL 63 dichloromethane was added PyBop (10.9mmol, 5.7g) at 0C, and the mixture stirred for 0.5h. Subsequently, 64 DIEA (21.87mmol, 3.61mL) and 25 4-methoxy-N-methylaniline (7.29mmol, 1.0g) were added to the mixture and then stirred at room temperature for another 8-9h (monitored by TLC). The resulting mixture was evaporated under reduced pressure and the residue was initially washed by 1N HCl and extracted with ethyl acetate (3×20mL). Then, the combined organic layer was washed with saturated sodium bicarbonate (3×50mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford corresponding crude intermediate 65 2 as yellow oil with a yield of 94%. 1H NMR (400MHz, DMSO-d6) delta 7.21 (d, J=8.4Hz, 3H), 7.15 (d, J=7.1Hz, 2H), 7.02 (d, J=8.4Hz, 2H), 6.85-6.75 (m, 2H), 4.15 (q, J=5.4Hz, 1H), 3.80 (s, 3H), 3.12 (s, 3H), 2.81-2.54 (m, 2H), 1.30 (s, 9H). 13C NMR (100MHz, DMSO) delta 172.21, 158.98, 155.74, 138.53, 136.13, 129.28, 128.47, 126.70, 115.21, 78.33, 55.94, 53.53, 37.86, 37.10, 28.65. ESI-MS: m/z 385.4 (M+1)+, C22H28N2O4 (384.2)
The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Wu, Gaochan; Zalloum, Waleed A.; Meuser, Megan E.; Jing, Lanlan; Kang, Dongwei; Chen, Chin-Ho; Tian, Ye; Zhang, Fangfang; Cocklin, Simon; Lee, Kuo-Hsiung; Liu, Xinyong; Zhan, Peng; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 478 – 492;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem