Potassium Hydroxide → (1, 1-dimethyl-2-(4-oxo-5-(2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)-carbamic acid tert-butyl ester

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Reaction Steps

A solution of dry powdered potassium hydroxide (0.23 g, 4.0 mmol) and (1,1-dimethyl-2-(4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)carbamic acid tert-butyl ester (0.49 g, 1.0 mmol) in DMSO (15 ml) was stirred for 0.5 h under an atmosphere of nitrogen. 5-(4'-Bromomethyl-biphenyl-2-yl)-N-(triphenylmethyl)tetrazole (0.59 g, 1.1 mmol) was added and the mixture was stirred for 1 h. A 10% aqueous solution of ammoniumchloride (30 ml), water (100 ml) and ethyl acetate (60 ml) were added and the phases were separated. The organic layer was dried (MgSO4), and the solvent was evaporated in vacuo. Purification by columm chromatography on silica gel (100 g) using heptane and ethyl acetate (2:3) as eluent afforded 0.45 g of (1, 1-dimethyl-2-(4-oxo-5-(2'-(N -triphenylmethyltetrazol-5-yl)biphenyl-4-ylmethyl)-2,3,4,5-tetrahydro- 1H-naphtho[2,1-b]azepin-3-ylcarbamoyl)ethyl)- carbamic acid tert-butyl ester.

Provenance & Evidence