Triethylamine → HCID 59828821, compound

Participants

Reaction Steps

To a mixture of 4-(2-aminothiazol-4-yl)-N-(tert-butoxycarbonyl)-benzylamine (2.98 g, 9.76 mmol) in DCM/dioxane (2:1, 150 mL) at room temperature, add triethylamine (2.0 mL, 15 mmol) and cyclopropanecarbonyl chloride (1.1 mL, 12 mmol). Stir at room temperature overnight and partition the reaction mixture between EtOAc (500 mL) and saturated aqueous NaHCO3 (250 mL). Dry the organic extract over Na2SO4, filter and concentrate in vacuo. Combine the residue with DCM and silica gel (12 g) and concentrate to a powder. Load powder on to a dry column attached to an Analogix® column (330 g) and purify by preparative liquid chromatography (0:1 to 1:4 EtOAc/hexane over 33 min, 1:4 EtOAc/hexane over 33 min, 1:4 to 1:1 EtOAc/hexane over 33 min, 1:1 EtOAc/hexane over 66 min; 35 mL/min) to afford the desired intermediate (2.381 g, 65%) as a yellow solid. MS (ES+) m/z: 374.2 (M+H)+.

Provenance & Evidence