Sodium triacetoxyborohydride → 3-[2(R)-(t-butyloxycarbonylamino)-3-(triphenylmethyl-mercapto)propylamino]-N-(2, 3-dimethylphenyl)benzamide

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Reaktionsschritte

To a solution of 2 (0.28 g) in 12 mL of 1,2-dichloroethane at 0° C. was added sodium triacetoxyborohydride (0.36 g) and N-t-butyloxycarbonyl-S-(triphenyl- methyl)cysteinal (0.35 g). The cooling bath was removed and the mixture was stirred for 4 h at 20° C. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a foam. NMR (300 MHz, CDCl3) δ 8.17 (1H, b), 7.46-7.18 (15H, m), 6.60 (1H, m), 3.13(2H, m,), 2.45(3H, m), 2.30 (3H, s), 2.18 (3H, s), 1.42 (9H, s).

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