tert-Butyldimethylsilyl chloride → HCID 9879821, compound

Participants

Reaction Steps

Into a solution of 4-(aminomethyl)amino benzoic acid (5.0 g, 33.1 mmol) in anhydrous THF (200 mL) were added DIEA (12.45 mL, 72.7 mmol) and tert-butyl dimethyl chlorosilane (5.48 g, 36.4 mmol). The resulting mixture was allowed to stir at rt for 1 hr and methyl 4-(chlorocarbonyl)benzoate (7.23 g, 36.4 mmol) was added neat. After overnight stirring at rt, the reaction mixture was quenched with HCl (0.1N, 250 mL) until pH=1. Extraction with EtOAc/THF (400 mL), drying over MgSO4, evaporation under vacuo gave the title compound as a white powder (7.0 g, 67%).

Provenance & Evidence