反应详情

tert-Butyl nitrite (2.2 ml, 18.6 mmol) and cuprous chloride (1.5 g) were suspended in anhydrous CH3CN (100 ml). Methyl 2-amino-4-(methoxymethyl)-1,3-thiazole-5-carboxylate (2.5 g) prepared as described in (Kennedy, Alan R. et al. Acta Crystallographica, Section C: Crystal Structure Communications (1999, C55 (7) 2) was added in one portion. The mixture was stirred at room temperature for 2 h and the temperature was raised to 70° C. for 1 h. The mixture was cooled to room temperature and filtered. The filtrate was poured into 6 N HCl, extracted with EtOAc, dried with MgSO4 and concentrated to a black oil. Flash purification on silica gel with gradient elution (hexane to EtOAc) yielded product as a yellow liquid (0.82 g). NMR: 3.31 (s, 3H), 3.85 (s, 3H), 4.71 (s, 2H).

1. temperaturethe temperature was raised to 70° C. for 1 h
2. temperatureThe mixture was cooled to room temperature
3. filtrationfiltered
4. additionThe filtrate was poured into 6 N HCl
5. extractionextracted with EtOAc
6. dry with materialdried with MgSO4
7. concentrationconcentrated to a black oil
8. customFlash purification on silica gel
9. washwith gradient elution (hexane to EtOAc)