Reacción #9183

Ecuación de reacción

ethyl-2-amino-4-methyl-thiazole-5-carboxylate

di-t-butyldicarbonate

→

title compound

Rendimiento 72.0%

Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

Rendimiento 72.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated in vacuo
2. 2
   Filtraciónfiltered through a pad of celite
3. 3
   LavadoThe filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was triturated with hexanes
7. 7
   FiltraciónThe solid was filtered
8. 8
   Otrodried in vacuo

Procedimiento

A suspension of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 100 mmol), di-t-butyldicarbonate (26.2 g, 120 mmol) and 4-dimethylaminopyridine (800 mg, 6.55 mmol) in dry tetrahydrofuran (300 mL) was stirred under nitrogen for 18 h. The solvent was evaporated in vacuo. The residue was suspended in dichloromethane (1 L) and filtered through a pad of celite. The filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine, dried (MgSO4), and concentrated in vacuo. The residue was triturated with hexanes. The solid was filtered and dried in vacuo to obtain the title compound (20 g, 72%) as a tan solid.

Fuente