Triethylamine → HCID 46193931, compound

Participants

Reaction Steps

0.17 ml (1.23 mmol) of triethylamine is carefully added to a solution containing 87 mg (0.45 mmol) of 3-(3-methyl-1H-imidazol-4-yl)propionic acid hydrochloride and 160 mg (0.49 mmol) of TBTU in 1 ml of DMF. After stirring for 60 minutes at ambient temperature, 200 mg (0.32 mmol) of (R)-2-amino-3-(4-methoxyphenyl)-1-(3-pentyl-3-phenylazetidin-1-yl)propan-1-one trifluoroacetate (cf. procedure 9-3) are added and the reaction medium is left to stir for three days. The reaction medium is treated with a 2 heptane/8 EtOAc mixture and a 1N aqueous solution of sodium hydroxide. The organic phase is dried over MgSO4, filtered and evaporated. The residue obtained is purified by silica chromatography (eluent 9 DCM/1 MeOH). 21 mg of N—[(R)-1-(4-methoxybenzyl)-2-oxo-2-(3-pentyl-3-phenylazetidin-1-yl)ethyl]-3-(3-methyl-3H-imidazol-4-yl)propionamide are obtained with a yield of 9%.

Provenance & Evidence