2-Aminothiazole → HCID 57657323, compound

Participants

Reaction Steps

A solution of Boc-Cha-OH (9.2 g, 34 mmol), DIEA (15 ml, 85 mmol) and BOP (16.5 g, 37 mmol) in DMF (80 ml) was maintained at ambient temperature for 40 minutes followed by the addition of thiazol-2-ylamine (3.4 g, 34 mmol). Reaction was maintained at ambient temperature for 2 hours. Reaction mixture was diluted with water (200 ml) and extracted with EtOAc (2×150 ml). Organic layer was washed with brine (100 ml), dried over anh. MgSO4 and evaporated in vacuum. Residue was subjected to flash chromatography on CombiFlash® Companion unit equipped with RediSep® flash column (normal phase, 35-60 micron average particle size silicagel, 40 g, Teledyne Isco); flow rate=35 ml/min; injection volume 2 ml; mobile phase A: hexane; mobile phase B: EtOAc; gradient 0-70% B in 1 h. Fractions containing the desired product were combined and concentrated in vacuum to provide target compound (8.89 g, 74%) as yellow oil. LC-MS [M+H] 354.4 (C17H27N3O3S+H, requires 354.49).

Provenance & Evidence