Hydrochloric Acid → Tert-butyl 1,3-thiazole-4-carboxylate

Temperatur

60 °C

To a solution of thiazole-4-carboxylic acid 7.1 (1 g, 7.2 mmol) and carbonyldiimidazole (6.3 g, 38.7 mmol) in commercial dry DMF (50 mL) under N2 was stirred at 50° C. for 20 min. Tert-butanol (8.6 g, 116.0 mmol) and DBU (5.8 mL, 38.7 mmol) were then successively added at once and the reaction was warmed at 60° C. for 48 h. The RM was then allowed to cool down to RT and the pH was adjusted to 4 with a solution of HCl (2M, ˜80 mL). The mixture was diluted with water (250 mL) and extracted with Et2O (3×100 mL). The combined org. layers were washed with brine (250 mL), dried over MgSO4, concentrated and purified on silica gel using DCM to afford title product as yellowish oil (47%). Yield: 3.37 g (47%). LCMS: P=98%, rt=3.65 nm, m/z=186.

1. temperatureto cool down to RT
2. extractionextracted with Et2O (3×100 mL)
3. washlayers were washed with brine (250 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. custompurified on silica gel

ORD-Eintrag

ord-beb5a80539924462b21bb4ef310f3bf3

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08871761B2