Reference of 149990-27-2, A common heterocyclic compound, 149990-27-2, name is tert-Butyl but-3-yn-1-ylcarbamate, molecular formula is C9H15NO2, 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 mixture of Cpd.4-5? (5.40 g, 12.9 mmol, 1.0 eq) and Cpd.2 (2.18 g, 12.9 mmol, 1.0 eq) in Et3N(110 mL) was added Cul (49.2 mg, 258 umol, 0.02 eq), PdCI2(PPh3)2 (181 mg, 258 umol, 0.02 eq) atC under N2 and stirred at 25 C for 16 hrs. TLC (petroleum ether/ethyl acetate = 1/1, Rf = 0.3) showthat the reaction was complete. Then aq.NH4CI (200 mL) was added, extracted with EtOAc (200mL*3), the combined organic layers were washed with brine, dried over Na2SO4 and filtered. Thefiltrate was concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluted with petroleum ether: EtOAc (10:1, 1:1) to give Cpd.4-6 (3.0048% yield) as yellow oil.1H NMR: ET5008-32-Plbl 400 MHz CDCI3 [17.41-7.34 (m, 1H), 7.23-7.06 (m, 3H), 4.97-4.87(m, 1H), 3.97 (s, 2H), 3.53 (t, i = 6.8 Hz, 2H), 3.43-3.33 (m, 2H), 2.72 (t, i = 8.0 Hz, 2H), 2.64 (i = 8.0 Hz,2H), 1.69-1.59 (m, 4H), 1.55-1.43 (m, 22H).
The synthetic route of 149990-27-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; OMEICOS THERAPEUTICS GMBH; MAX DELBRUeCK-CENTRUM FUeR MOLEKULARE MEDIZIN; FISCHER, Robert; SCHUNCK, Wolf-Hagen; MUeLLER, Dominik; WESSER, Tim; KONKEL, Anne; LOSSIE, Janine; (115 pag.)WO2017/168007; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics