Electric Literature of 86770-74-3 , The common heterocyclic compound, 86770-74-3, name is 2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethanol, molecular formula is C8H19NO4, 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.
To a solution of 1-7 and HATU (147 mg) in DMF (1 mL) was added dropwise DIEA (135 muL) and tetraethylene glycol monoamine (45 muL). After stirring at room temperature for 5 h, the reaction was quenched by 10% aqueous citric acid, and the reaction mixture was extracted with EtOAc. The organic phase was washed with 1N HCl, brine, and saturated NaHC03. After drying over MgSO4 and filtration, solvent was removed with a rotary evaporator, and the mixture was purified by silica gel chromatography (DCM: MeOH=30: 1) to afford 1-27 in 70% yield. Q-TOF LC/MS m/z 609.3797 [M+H]+ (calcd. 608.37 for C32H52N2O9 [M]+); 1HNMR (400 MHz, CDCl3) delta -0.45 (1H, m), 0.685 (1H, m), 0.825 (6H, m), 1.13 (9H, s), 1.27-1.64 (6H, m), 1.94 (1H, m), 2.05 (1H, m), 2.64 (2H, m), 3.38-3.91 (16H, m), 4.07 (1H, t, J=8 and 12 Hz ), 4.25 (1H, m), 4.99 (1H, m), 6.35-7.06 (4H, aromatic H); 13C NMR (100 MHz, CDC13) delta 21.45, 24.12, 25.92, 28.20, 30.00, 31.10, 38.40, 39.51, 40.65, 49.28, 50.18, 52.77, 61.65, 69.98, 70.22, 70.60, 70.90, 72.60, 73.92, 80.30, 120.40, 123.35, 129.95, 132.23, 132.46, 159.12, 171.62, 173.23, 174.34.
The synthetic route of 86770-74-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; YALE UNIVERSITY; THE UNITED STATES OF AMERICA as represented by THE DEPARTMENT OF VETERANS AFFAIRS; SADEGHI, Mehran; YE, Yunpeng; KIM, Hye-Yeong; HUANG, Henry (Yiyun); TOCZEK, Jakub; (85 pag.)WO2017/177144; (2017); A1;,
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