Application of 6298-96-0, These common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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.
Synthesis of Compound 117; To a solution of betulinic acid (0.18 g, 0.394 mmol) in dry DMF (2 mL) was added EDCl-HCl (0.113 g, 0.5912 mmol), HOAt (0.054 g, 0.3941 mmol) and iPr2NEt (0.21 mL, 1.182 mmol) at ambient temperatures. After stirring for 10 minutes, commercially available (S)-1-(4-methoxy-phenyl)-ethylamine (0.09 g, 0.59 mmol) was introduced and the resulting mixture was allowed to stir for 18 h at ambient temperatures. After this time the mixture was transferred onto aqueous 1% HCl, the solid collected by filtration, and then purified by medium pressure liquid chromatography (SiO2, 0-50% EtOAc-hexane) to give intermediate amide (168 mg, 72% yield). Analytical data; 1H-NMR (400 MHz, d6-DMSO) delta 7.76 (d, J=7.6 Hz, 1H), 7.20 (d, J=8.7 Hz, 2H), 6.83 (d, J=8.7 Hz, 2H), 4.95-4.85 (m, 1H), 4.64 (d, J=2.3 Hz, 1H), 4.53 (bs, 1H), 4.26 (d, J=5.0 Hz, 1H), 3.72 (s, 3H), 2.90-3.05 (m, 2H), 2.30-2.20 (m, 1H), 1.90-1.00 (m, 25H), 1.00-0.75 (m, 10H), 0.71 (s, 3H), 0.63 (s, 3H), 0.57 (s, 3H); LC-MS (ESI): 590.4917 (M+H)+. To a solution of the aforementioned amide (0.153 g, 0.259 mmol) in dry pyridine (1 mL) was added commercially available 2,2-dimethylsuccinic anhydride (0.166 g, 1.297 mmol) and 4-DMAP (0.032 g, 0.259 mmol). The mixture was then heated at reflux under an inert atmosphere. After heating overnight (18 h) the mixture was diluted with toluene, concentrated under reduced pressure, recovered in CH2Cl2 and washed with 10% HCl. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Purification by medium pressure liquid chromatography (SiO2, 0-20% MeOH-CH2Cl2) provided 117 (143 mg, 77% yield). See Table 3 for appropriate analytical data.
The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Myriad Genetics, Incorporated; US2008/207573; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem