Tag: 873397-34-3

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.873397-34-3,Tetrahydro-2H-pyran-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Into a 8-mL round-bottom flask, was placed ethyl (S)-5-methyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine-8-carboxylate (from the second eluting isomer of Example 47 Step 5) (200 mg, 0.85 mmol, 1 equiv) in DMF (4 mL), HATU (388 mg, 1.02 mmol, 1.2 equiv), DIEA (330 mg, 2.55 mmol, 3 equiv) and oxane-3-carboxylic acid (166 mg, 1.28 mmol, 1.5 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water. The resulting solution was extracted with EtOAc (3¡Á5 mL). The combined organic layers were washed with brine (2¡Á5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc/pet. ether, 1:3) to afford the racemic mixture of the title compounds as a yellow oil (150 mg). The racemate was separated by Chiral-Prep-HPLC (Column Chiralpak IC, 5 mum, 2¡Á25 cm; Mobile Phase A:hexanes; Mobile Phase B: EtOH; Gradient: 30percent B for 21 min; Flow rate: 20 mL/min; Detector, UV 254, 220 nm) to afford the single isomers of title compounds as yellow oils (first eluting isomer: 20 mg, 7percent yield; second eluting isomer: 20 mg, 7percent yield). MS: (ES, m/z): 348 [M+H]+.

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Reference£º
Patent; Forma Therapeutics, Inc.; Zheng, Xiaozhang; Ng, Pui Yee; Han, Bingsong; Thomason, Jennifer R.; Zablocki, Mary-Margaret; Liu, Cuixian; Davis, Heather; Rudnitskaya, Aleksandra; Lancia, JR., David; Bair, Kenneth W.; Millan, David S.; Martin, Matthew W.; (190 pag.)US2016/222028; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thionyl chloride (0.17 mL, 2.4 mmol) was added to a stirred solution of tetrahydro-pyran-3- carboxylic acid (0.26 g, 2.0 mmol) in DCM (4 mL) and DMF (0.1 mL). The mixture was stirred at room temperature for 30 min then Meldrum’s acid (0.576 g, 4.0 mmol) was added and the mixture was left to stir at room temperature for 1 hour. The reaction mixture was washed with a 2 N HC1 (aq) solution and evaporated under reduced pressure. The residue was dissolved in methanol and heated to reflux for 6 h. The mixture was then concentrated under reduced pressure to give the title compound (0.27 g, 75percent yield) which was used in the next step without further purification.

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Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics