59418-09-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59418-09-6,Methyl 4-thiazolecarboxylate,as a common compound, the synthetic route is as follows.
Methyl(R)-2-(3-((tert-butoxycarbonyl)(methyl)amino)-4-methylpentanoyl)thiazole-4- carboxylate (3e): To a stirred solution of aldehyde 1 (80 mg, 0.35 mmol) and methyl thiazole-4-carboxylate 2e (25 mg, 0.17 mmol) in anhydrous benzene (1.0 mL) at 25 C were added portion-wise over 15 min TMSN3 (0.05 mL, 0.35 mmol) followed by phenyliodinebis(trifluoroacetate) (PIFA, 150 mg, 0.35 mmol). After stirring for 16 h at 25 C, TLC analysis indicated complete consumption of aldehyde 1, while unreacted methyl thiazole-4-carboxylate 2e was still present in the reaction mixture. Consequently, more aldehyde 1 (80 mg, 0.35 mmol), TMSN3 (0.046 mL, 0.35 mmol) and PIFA (150 mg, 0.35 mmol) were added portion-wise over 15 min at 25 C and stirring was continued for an additional 12 h. The reaction mixture was cooled to 0 C and quenched with Et3N (0.2 mL). The solvent was removed under reduced pressure and the resulting residue was purified by flash column chromatography (silica gel, 10?40% EtOAc in hexanes) to produce ketone 3e (7.7 mg, 12% yield) as a colorless oil. 3e: Rf- 0.35 (silica gel, 25% EtOAc in hexanes); [cc]D – 12.0 (c = 1.0, CHCI3); FT-IR (neat) f^,: 2960, 2921, 2851, 1743, 1690, 1460, 1366, 1335, 1248, 1218, 1145, 995, 770 cm 1; NMR: (CDCI3, 600 MHz) delta = 8.42 (d, J = 13.4 Hz, 1H), 4.27 (s, 1H), 3.97 (d, J = 4.3 Hz, 3H), 3.66 – 3.08 (m, 2H), 2.72 (d, J = 1.7 Hz, 3H), 1.88 (dt, J = 16.5, 7.6 Hz, 1H), 1.34 (d, J = 15.0 Hz, 9H), 1.03 (dd, J = 16.7, 6.6 Hz, 3H), 0.89 (dd, J = 6.7, 2.6 Hz, 3H); 13C NMR: (CDCI3, 150 MHz) delta = 192.0, 167.2, 161.2, 155.8, 148.3, 133.4, 79.5, 59.7, 58.8, 52.6, 39.8, 31.1, 28.2, 20.2, 19.6; HRMS calcd for Ci7H26N205S [ +Na+] 393.1460 found 393.1448.
The synthetic route of 59418-09-6 has been constantly updated, and we look forward to future research findings.
Reference：
Patent; WILLIAM MARSH RICE UNIVERSITY; NICOLAOU, Kyriacos, C.; VOURLOUMIS, Dionosios; YIN, Jun; ERANDE, Rohan; MANDAL, Debashis; KLAHN, Philipp; (322 pag.)WO2016/138288; (2016); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica