tert-butyl (2S)-2-amino-3-phenylpropanoate → (S)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Participants

Reaction Steps

Following the 13a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 13b as colorless oil; (154.68 mg, 90.1%). [α]D25: +15.7 (c=0.26, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.08 (d, J=8.1 Hz, 1H), 8.03 (s, 1H), 7.96-7.91 (m, 1H), 7.80-7.76 (m, 1H), 7.39-7.18 (m, 6H), 4.98-4.92 (m, 1H), 3.36-3.15 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 172.17, 163.11, 161.48, 159.86, 142.28, 139.43, 137.51, 136.19, 129.23, 128.32, 126.89, 126.76, 126.60, 124.43, 114.09, 108.67, 54.12, 37.02; HRMS (ESI): calcd for: C18H14FNO3S [M−H]−=342.0606, obsd [M−H]−=342.0593.

Provenance & Evidence