Triethylamine → HCID 22879396, compound

Participants

Reaction Steps

A mixture of 1.98 g (3.06 mmol) of (S)-1-(tert-butoxycarbonyl)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]imidazole-4-propionic acid, 0.58 g (2.55 mmol) of (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol, 0.5 g (3.06 mmol) of 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, 0.42 ml (3.07 mmol) of triethylamine and 1.16 g. (3.06 mmol) of HBTU in 30 ml of dimethylformamide is stirred at room temperature under argon for 2 hours. Subsequently, the dimethylformamide is evaporated in a high vacuum and the residue is taken up in 60 ml of ethyl acetate. The ethyl acetate solution is extracted with 30 ml of cold 2N sodium bicarbonate solution and the aqueous phase is back-extracted twice with 60 ml of ethyl acetate. The combined organic phases are washed in sequence with 30 ml of cold, saturated ammonium chloride solution, 30 ml of cold 2N sodium bicarbonate solution and 30 ml of saturated sodium chloride solution. The organic phase is dried over sodium sulphate and evaporated under reduced pressure. There are obtained 2.82 g of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-Boc-imidazole-4-propionamide as a pale yellow foam.

Provenance & Evidence