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

Participants

Reaction Steps

Following the 4a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 4b as a white powder; (175.31 mg, 92.8%). [α]D25: +15.5 (c=0.38, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.03-7.77 (m, 3H), 7.44-7.25 (m, 6H), 5.03-4.97 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 163.90, 160.62, 159.50, 139.01, 136.65, 133.57, 129.50, 128.40, 126.88, 124.94, 115.15, 114.82, 109.31, 108.96, 54.06, 36.79; HRMS (ESI): calcd for: C18H13ClFNO3S [M+H]+=378.0361, obsd [M+H]+=378.0352.

Provenance & Evidence