Electric Literature of 85006-25-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 85006-25-3 name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
To an ice cooled (0 C) solution of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (4.90 g, 21.01 mmol) in anhydrous DMF (30 mL) under nitrogen was added portion-wise 60% sodium hydride in mineral oil (540 mg, 22.5 mmol) and stirred for 30 min. The reaction mixture was treated with dropwise addition of a solution of [N-3-(3-fluoro -4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl methane sulfonate (5.90 g, 15.8 mmol) in DMF (70 mL). The reaction mixture was stirred to room temperature for 64 h. The reaction mixture was diluted with water (210 mL) and extracted with ethyl acetate (3 * 100 mL) and the EtOAc extract was diluted with hexane (60 mL) and washed with water, brine, dried (Na2SO4), filtered and concentrated to give the crude as a brown oil. Silica gel column chromatography eluted with EtOAc-Hexane 2:1 gave the titled compound 24 [17] as a pale yellow viscous oil (6.27 g, yield, 77.8%). 1H-NMR (DMSO-d6, 600 MHZ): delta 7.51 (dd, 1H, J = 15.0 Hz, 2.5 Hz, phenyl H), 7.19 (dd, 1H, J = 8.8 Hz, 2.5 Hz, phenyl H), 7.09 (t, 1H J = 9.6 Hz, phenyl H), 4.87 (m, 1H, oxazolidinone H), 4.15 (t, 1H, J = 4.6 Hz, oxazolidinone H), 3.97 (m, 1H, oxazolidinone H), 3.82 (m, 1H, methylene H), 3.72-3.76 (br t, 5H, morpholine H and methylene H), 2.97 (br t, 4H, morpholine H), 1.41-1.48 (br, 18H). MS 511.2 (M+).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (tert-butoxycarbonyl)oxycarbamate, and friends who are interested can also refer to it.
Reference:
Article; Phillips, Oludotun A.; D’Silva, Roselyn; Bahta, Teklu O.; Sharaf, Leyla H.; Udo, Edet E.; Benov, Ludmil; Eric Walters; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 120 – 131;,
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