tert-butyl (2S)-2-amino-3-phenylpropanoate → (S)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Participants

Reaction Steps

Following the 8a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 8b as a white powder; (93.51 mg, 94.5%). [α]D25: +22.3 (c=0.43, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.80 (s, 1H), 7.64-7.51 (m, 3H), 7.34-7.24 (m, 5H), 5.16-5.10 (m, 1H), 3.43-3.28 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 175.44, 160.03, 153.01, 151.93, 149.64, 148.62, 135.14, 133.75, 133.28, 129.45, 128.83, 127.55, 188.89, 110.98, 110.79, 110.53, 54.04, 37.28; HRMS (ESI): calcd for: C18H12ClF2NO3S [M−H]−=394.0122, obsd [M−H]−=394.0127.

Provenance & Evidence