tert-butyl N-((1S)-1-cyanoethyl)carbamate → (S)-4-(3-(benzyloxy)benzyloxy)-N-(1-cyanoethyl)benzamide

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Reaction Steps

General procedures D and E were used to deprotect 0.45 mmols of (S)-tert-butyl 1-cyanoethylcarbamate and couple to 0.45 mmols of the acid 36. After purification by flash chromatography, 0.23 mmols of the title product was recovered. 1H NMR (500 MHz, CDCl3) δ 7.78-7.72 (m, 2H), 7.47-7.42 (m, 2H), 7.41-7.37 (m, 2H), 7.36-7.29 (m, 2H), 7.06 (s, 1H), 7.02 (s, 1H), 7.01-6.98 (m, 2H), 6.95 (dd, J=2.5, 8.2, 1H), 6.46 (s, 1H), 5.15 (dd, J=7.6, 14.9, 1H), 5.09 (s, 2H), 5.07 (s, 2H), 1.65 (d, J=7.2, 3H). 13C NMR (75 MHz, CDCl3) δ 191.04, 163.88, 159.36, 137.82, 136.98, 132.24, 130.09, 128.86, 128.29, 127.74, 120.05, 115.39, 114.79, 114.14, 70.25.

Provenance & Evidence