tert-Butanol → Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

Participants

Reaction Steps

A solution of monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate (3.0 g), diphenyl-phosphoryl azide (2.51 g) and triethylamine (1.3 ml) in dry t-butanol (25 ml) was stirred at room temperature for 15 minutes and then heated under reflux for 20 hours. The solution was evaporated and the residue was partitioned between ether and wateT. The ether layer was separated, dried (MgSO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane gave the title compound as a gum (2.41 g), Rf 0.2(SS 3). N.M.R. δ(CDCl3): 1.23(3H,t), 1.44(9H,s), 2.58(2H,t), 2.72(2H,t), 2.88(2H,t), 3.32(2H,m), 3.89(2H,s), 4.10(2H,q), 4.50(1H,br), 6.82-6.90(3H), 6.94-7.0(2H,m), 7.09-7.15(2H,m).

Provenance & Evidence