Methyl 6-bromo-5-oxohexanoate → Methyl 4-(2-amino-1,3-thiazol-4-yl)butanoate

Participants

Reaction Steps

Bromide 1-2 (3.45 g, 15.5 mmol) and thiourea (1.4 g, 18 mmol) were combined in 77 mL EtOH and heated to reflux. After disappearance of 1-2 the EtOH was removed by rotary evaporation and the residue was diluted with EtOAc, washed with water and brine, then dried (MgSO4), filtered and concentrated. The pH of the aqueous phase was adjusted to 7, and the solution was re-extracted with EtOAc (2×). These organic extracts were washed with brine, dried (MgSO4), filtered and concentrated, combined with the first organic residues, then purified by flash chromatography (silica, EtOAc) providing aminothiazole 1-3 as a white solid.

Provenance & Evidence