With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.921927-88-0,Methyl 2-formylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.
(0283) A solution of DIEA (15.8 mL, 110 mmol) in anhydrous ether (200 mL) was cooled to -78 C. n-BuLi (2M, 55 ml, 110 mmol) was added drop wise. The resulting mixture was warmed to 0 C. then continued to be stirred for 45 min at 0 C. The mixture was recooled to -78 C. and a solution of sulfinamide 51 (10 g, 52 mmol) in ether (100 mL) was added dropwise. The reaction mixture and stirred at -78 C. for 1 h. Chlorotitanium triisopropoxide (31.7 g, 121 mmol) was added and resulting reaction mixture was continue stirred at -78 C. for 1 h. Compound 48 (9 g, 52 mmol) was added in one portion and the resulting reaction mixture was continue stirred at -78 C. overnight. The reaction mixture was quenched with 20% acetic acid in THF and allowed to warm to RT. Water (2.5 mL) was added and the resulting solution was filtered through a pad of CELITE. The pad was washed thoroughly with ethyl acetate. The filtrate was extracted with ethyl acetate (3×). The combined organic extracts were washed 1× with saturated aq. NaCl. The organic fraction was dried with anhydrous Na2SO4 and filtered. The filtrate concentrated in vacuo. The residue was purified by flash chromatography (230-400 mesh silica) with a gradient of 15-20% ethylacetate-petroleum ether mixture to afford methyl 2-((R,E)-3-(((R)-tert-butylsulfinyl)imino)-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate 52 (9.0 g, 47%) as a pale yellow viscous oil. 1H NMR (CDCl3) (400 MHz) delta 1.17-1.06 (m, 6H), 1.23 (s, 9H), 2.88-2.84 (m, 1H), 3.37-3.34 (m, 2H), 3.94 (s, 3H), 5.17-5.09 (m, 1H), 6.63 (d, 1H, J=13.2 Hz), 8.16-8.13 (d, 1H, J=13.2 Hz); MS (ESI+) m/z 361.0 (M+H)+.
921927-88-0, As the paragraph descriping shows that 921927-88-0 is playing an increasingly important role.
Reference：
Patent; Bristol-Myers Squibb Company; PEREZ, Heidi L.; WEI, Donna; BORZILLERI, Robert M.; GANGWAR, Sanjeev; SCHROEDER, Gretchen M.; CHENG, Heng; SCHMIDT, Robert J.; (58 pag.)US2016/130299; (2016); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica