Oxalyl chloride → {2-[3-Chloro-5-(3-fluorophenyl-(3-tetrazol-2-yl-propyl)-carbamoyl)-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Participants

Reaction Steps

2M Oxalyl chloride solution in dichloromethane (0.11 ml) and dry DMF (0.002 ml) were added to a stirred suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.060 g) in dry dichloromethane (1 ml) under nitrogen. After 5 min, DIPEA (0.090 ml) was added followed after a further 40 min by 3-fluorophenyl-(3-tetrazol-2-yl-propyl)-amine (0.066 g) and DMAP (0.002 g). After 3 days the solvent was evaporated and the residue was purified by flash chromatography eluting with dichloromethane:methanol (98:2 v/v) to give the title compound as a green foam (0.079 g).

Provenance & Evidence