Triethylamine → HCID 19010158, compound

Participants

Reaction Steps

To 50 ml of ethyl acetate, there were added 4.27 g (24.4 mmol) of N-(tert-butoxycarbonyl)glycine and 5.03 g (24.4 mmol) of N,N'-dicyclohexyl carbodiimide and stirred at room temperature for 30 minutes. The obtained solution was cooled in an ice bath and 3.00 g (24.4 mmol) of 6-amino-m-cresol and 2.51 g (24.4 mmol) of triethylamine were added thereto. After putting back to room temperature, the mixture was stirred for 12 hours. After the completion of the reaction, 50 ml of N,N-dimethylformamide was added thereto and the crystals thus precipitated were filtered and washed with 20 ml of N,N-dimethylformamide. The filtrate was combined with the washing liquor and the solvent was distilled off therefrom under reduced pressure to thereby give a brown solid. This product was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 300 g; eluent: 3% methanol-chloroform). From the 900-1,300 ml fraction, the solvent was distilled off under reduced pressure and 20 ml of chloroform was added thereto to cause thereby crystallization. After filtering and drying, 2.00 g (7.1 mmol) of N-(2-hydroxy-4-methylphenyl)-tert-butoxycarbonylaminoacetamide was obtained as yellow crystals. The yield was 29%.

Provenance & Evidence