Related Products of 5961-59-1, These common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, 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.
HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N- methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at RT for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (60 mL) and 1/2 sat. NaHCO3 (aq) (60 mL). The organic component was washed with brine (40 mL), dried (Mg504), filtered, concentrated and purified using a Biotage Horizon (80g5i02, 10-40% EtOAc/hexanes) to yield (5)-tert-butyl (1-((4- methoxyphenyl)(methyl)amino)- 1 -oxo-3 -phenylpropan-2-yl)carbamate (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 mm; mlz = 385.3 [M+H]. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 pm. Solvent A = 95% Water:5% Acetonitrile:10 miVi NH4OAc. Solvent B = 5% Water:95% Acetonitrile:10 miViNH4QAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time= 4 mm. Wavelength = 220). ?H NMR (400MHz, CDC13) oe 7.25 – 7.20 (m, 3H),7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (q, J=7.4 Hz, 1H), 3.83 (s, 3H),3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s,9H).
The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PENDRI, Annapurna; LI, Guo; BENDER, John A.; YANG, Zhong; WANG, Alan Xiangdong; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; MEANWELL, Nicholas A.; GENTLES, Robert G.; WO2015/61518; (2015); A1;,
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