1,2-Dichloroethane → 1,1-Dimethylethyl 9-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 1,1-dimethylethyl 9-[(hydroxyamino)(imino)methyl]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 65) (500 mg, 1.627 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (384 mg, 1.790 mmol), EDC (468 mg, 2.440 mmol) and HOBT (299 mg, 1.952 mmol) in DMF (5 ml) was stirred at RT overnight then heated at 120° C. for 3 hrs. The reaction mixture was cooled, diluted with EtOAc/water and the organics dried over magnesium sulfate and evaporated. Purified by flash chromatography eluting with EtOAc/iso-hexane 1:3 to give the title compound (320 mg) as a white solid. MS (ES): C25H2835ClN3O5 requires 485; found 486 [M+H]+.

Provenance & Evidence