4-Nitrobenzoyl chloride → HCID 68906871, compound

Participants

Reaction Steps

To a solution of (2RS,3RS)-3-indol-1-yl-3-phenyl-propane-1,2-diol (EXAMPLE 1, step 1, 1.83 g, 6.9 mmol) in anhydrous pyridine (25 mL), p-nitrobenzoyl chloride (1.3 g, 6.9 mmol) in 1 mL of pyridine was added at −10° C. dropwise. After stirring for 30 minutes, the reaction mixture was cooled with an ice bath and quenched with water and a 2N aqueous solution of hydrochloric acid until the solution was pH=3 and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to give (2RS,3RS)-4-nitro-benzoic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester quantitatively as a yellow solid. MS (ESI) m/z 417 ([M+H]+).

Provenance & Evidence