Category: 921927-88-0

921927-88-0, Methyl 2-formylthiazole-4-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

921927-88-0, Lithium diisopropyl amide (?LDA,? 60 mL, 108 mmol, 1 .8M) was added to 200 mL of ether at -78 C. followed by the addition of sulfinimine 7 (18.9 g, 100 mmol) in 200 mLether and the resultant reaction mixture was stirred for 40 mi C1Ti(OiPr)3 (203 mmol, 48.4 mL) was added to the reaction mixture and the solution was stirred for 60 mm. A solution of methyl 2-formylthiazole-4-carboxylate 4 (12.5 g, 72.6 mmol) in 180 mL of THF was added slowly to thereaction mixture. Afier another 2 h at -78 C., a mixture of acetic acid and THF (?A v/v, 4.9 mL) was added. The mixturewas warmed to 5 C. over 1 h and then poured into brine solution. The desired product was then extracted from the brine solution with ether and EtOAc solution. The organic phase was then dried over anhydrous MgSO4, filtered and evaporated. The residue was passed through 2 columns (DCM:EtOAc and hexane:EtOAc) to give compound 8 (19.6 g, 54 mmol, 75%) as an oil. MS (ES+) mlz, calculated: m+1, 361.12. found, 361.

The synthetic route of 921927-88-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; E. R. SQUIBB & SONS, L.L.C.; Cheng, Heng; Gangwar, Sanjeev; Cong, Qiang; (82 pag.)US9226974; (2016); B2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

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