Synthetic Route of 13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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 stirred solution of 3-butyl-3-ethyl-8-hydroxy-2-methyl-7-(methylthio)-5-phenyl-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide (Intermediate 152; 200 mg, 0.46 mmol) in dry THF (3 mL), DABCO (5.10 mg, 0.05 mmol) and tert butyl propiolate (0.1 mL, 0.7 mmol) were added at room temperature, and the reaction mixture was stirred for 1 hour at room temperature. After completion of the reaction (monitored by LCMS), the reaction mixture was diluted with ice-cold water (10 mL). The aqueous layer was extracted with EtOAc (2¡Á10 mL). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum. The resulting crude material was purified by Isolera column chromatography (eluent: 6% EtOAc in hexane; silica gel: 230-400 mesh) to afford the title compound. Yield: 75% (190 mg, white solid). H NMR (400 MHz, DMSO-d6): delta 7.61 (d, J=12.4 Hz, 1H), 7.38 (t, J=8.0 Hz, 3H), 7.30 (d, J=7.6 Hz, 2H), 7.12 (t, J=7.2 Hz, 1H), 6.46 (s, 1H), 5.31 (d, J=12.4 Hz, 1H), 4.12 (s, 2H), 2.88 (s, 3H), 2.08 (s, 3H), 1.92-1.86 (m, 1H), 1.82-1.76 (m, 1H), 1.55-1.43 (m, 10H), 1.19-1.08 (m, 5H), 0.83-0.62 (m, 6H). LCMS: (Method A) 505.2 (M+-tBu+H), Rt. 3.65 min, 97.40%.
The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Albireo AB; Gillberg, Per-Goeran; Mattsson, Jan; Starke, Ingemar; Kulkarni, Santosh S.; (152 pag.)US2019/367467; (2019); A1;,
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