1,2-Dichloroethane → tert-butyl[(R)-1-(4-methoxy-benzyl)-2-oxo-2-(3-pentyloxy-3-o-tolylazetidin-1-yl)ethyl]carbamate

Participants

Reaction Steps

2.93 g (9.93 mmol) of (R)-2-tert-butoxy-carbonylamino-3-(4-methoxyphenyl)propionic acid are dissolved in 10 ml of DMF. 2.08 g (10.9 mmol) of EDC, 1.47 g (10.9 mmol) of HOBt and a solution of 3.45 g (9.93 mmol) of 3-pentoxy-3-phenylazetidine trifluoro-acetate in 15 ml of DMF are then added. 7 ml (40.2 mmol) of DIEA are added. The reaction medium is stirred at ambient temperature for 2 h 30 and then extracted with ethyl acetate. The organic phase is washed with 1N sodium hydroxide and then dried over magnesium sulphate, filtered and evaporated. The crude product obtained is purified by silica gel chromatography (eluent 6/4 heptane/ethyl acetate). 2.83 g in the form of a white powder are obtained with a yield of 56%.

Provenance & Evidence