Chlorosuccinimide → 2-(2-Boc-amino-5-chlorothiazol-4-YL)-2-oxoacetic acid

Participants

Reaction Conditions

Reaction Steps

To a suspention of 2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxoacetic acid (23.5 g, 86 mmol) in 1,4-Dioxane (200 mL) was added NCS (12.22 g, 91 mmol) portionwise. The mixture was stirred at 40° C. for 2.5 h. The mixture was cooled to r.t. and filtered to remove the insoluable material. The filtrate was concentrated under vacuum. The residue was taken with Et2O and filtered. The filtrate was diluted with EtOAc and washed with water and brine. The organic solution was dried over sodium sulfate, filtered and concentrated. To the oily residue was added n-hexane and Et2O, and the mixture was concentrated in vacuo. After trituration, 2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)-2-oxoacetic acid (22.8 g, 74.3 mmol, 86% yield) was obtained as a light yellow solid. LCMS: (M+Na)+: 329.0.

Provenance & Evidence