A common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, molecular formula is C6H13NO2, 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. 16066-84-5.
To a suspension of sodium hydride (0.056g, 1.41 mmol) in DMF (3 mL) was added a solution of methylcarbamic acid t-butyl ester (0.184 g, 1.41 mmol) in DMF (2 mL). After stirring 1 hr, a solution of 3-(3-chloropropyl)-7-fluoro-1 -phenyl-1 H-4,2,1 – benzoxathiazine 2,2-dioxide (0.25 g, 0.72 mmol) in DMF (4 mL) was added. The mixture was stirred for 2 hr then poured into 2N HCI and extracted twice with ethyl acetate. The organic layers are dried over magnesium sulfate then concentrated and the residue purified by Sitheta2 column chromatography (10-35% gradient ethyl acetate/hexane). The purified residue was then dissolved in 5 mL of 2N HCI in ether and 0.1 mL of MeOH and the solution allowed to stand 18 hr whereupon crystals formed. The crystals were collected by filtration to yield 3-(7-fluoro-2,2-dioxido-1 – phenyl-1 H-4,2,1-benzoxathiazin-3-yl)-N-methylpropan-1 -amine hydrochloride (0.159): MS (ES) m/z 350.9;HPLC purity 100.0% at 210-370 nm, 7.4 minutes; Xterra RP18, 3.5 mu, 15O x 4.6 mm column, 1.2 mL/minutes. 85/15-5/95 (ammonium formate buffer pH =3.5/ACN+MeOH) for 10 minutes, hold 4 minutes.HRMS: calculated for Ci7H19FN2O3S + H+, 351.11732; found (ESI, [M+H]+), 351.1161.
The synthetic route of tert-Butyl methylcarbamate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; WYETH; WO2008/73956; (2008); A2;,
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