N-Benzyloxycarbonyl-beta-alanine → HCID 90985399, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-carbobenzoxy-β-alanine (20 mg, 0.090 mmol) in dichloromethane (2 ml) were added o-benzotriazol-1-yl-tetramethyluronium hexafluorophosphate (65 mg, 0.171 mmol), 1-hydroxybenzotriazole (15 mg, 0.111 mmol), and diisopropylethylamine (0.040 ml, 0.229 mmol). After 5 min, 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-(piperidin-4-ylmethyl)benzamide (30 mg, 0.075 mmol, INTERMEDIATE 15) was added and the mixture was stirred overnight at 25° C. The mixture was diluted with saturated sodium bicarbonate solution (10 ml) and dichloromethane (10 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (2×10 ml). The combined organics were washed with 10 ml of brine, dried (sodium sulfate), and concentrated. The residue was purified by flash chromatography on a Biotage Horizon, 25S column, eluting with 1 column volume of 100% dichloromethane followed by a gradient of 0 to 50% methanol in dichloromethane over 10 column volumes. The resulting mixture was repurified by preparative thin-layer chromatography, eluting with 5% methanol in dichloromethane provide the title compound (24.8 mg, 0.041 mmol, 54.8% yield). Mass spectrum (ESI) 630.1 (M+1).

Provenance & Evidence