1746-77-6,Some common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, molecular formula is C4H9NO2, 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 isopropyl carbamate (15.85 g, 154 mmol) in anhydrous THF (150 mL) in a flame-dried flask at -78 C was added crotonoyl chloride (14.16 mL, 146 mmol), followed by LiHMDS (300 mL, 1.0 M in THF). After 30 minutes of stirring at -78 C, solution was permitted to warm to RT and stir at RT overnight. Reaction was quenched via addition of sat. aq. NH4Cl (200 mL). Solution was extracted with EtOAc (3 x 75 mL). (0759) Combined organics were washed with sat NaCl and dried with MgSO4, filtered and concentrated under reduced pressure. Crude product was purified via automated normal phase chromatography (23% EtOAc in hexanes) to provide the desired imide as a white solid (12.3 g, 64% yield). mp 91 C. LCMS/UPLC (method: formate) retention time 0.82 min, [M + H]+ = 172.27.1H NMR (400 MHz, CDCl3) delta 7.55 (s, 1H), 7.14 (dq, J = 15.3, 6.9 Hz, 1H), 6.86 (dq, J = 15.2, 1.7 Hz, 1H), 4.99 (p, J = 6.3 Hz, 1H), 1.94 (dd, J = 6.9, 1.7 Hz, 3H), 1.30 (d, J = 6.3 Hz, 6H).13C NMR (126 MHz, CDCl3) delta 166.03, 151.36, 146.34, 122.94, 70.23, 21.78, 18.40.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isopropyl carbamate, its application will become more common.
Reference:
Patent; ST. JUDE CHILDREN’S RESEARCH HOSPITAL; GUY, R., Kip; SLAVISH, P., Jake; SHADRICK, William, Robert; YOUNG, Brandon, M.; BOYD, Vincent, A.; BHARATHAM, Nagakumar; PRICE, Jeanine, E.; SHELAT, Anang; (324 pag.)WO2018/111805; (2018); A1;,
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