N-(tert-butoxycarbonyl)glycine → Methyl 3'-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1'-biphenyl]-3-carboxylate

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Reaction Steps

To a mixture of 3′-amino-[1,1′-biphenyl]-3-carboxylic methyl ester (1.14 g) and N-(tert-butoxycarbonyl)glycine (0.879 g) in methylene chloride (20 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g). The mixture was stirred for 3 h at room temperature, then washed twice with 1 N aqueous HCl, twice with saturated aqueous sodium bicarbonate and once with brine. The mixture was dried over sodium sulfate, filtered and concentrated to give a foam. Purification by silica gel chromatography eluting with 7:3 hexane/ethyl acetate gave 1.6 g of the title compound as a colorless oil. Electrospray MS (positive ion): (M+Na) 407.0.

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