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

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Reaction Steps

Following the 5a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 5b as a yellow powder (99.57 mg, 93.1%). [α]D25: +24.7 (c=0.36, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 8.09 (s, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.69-7.61 (m, 2H), 7.36-7.25 (m, 5H), 7.04 (s, 1H), 5.15-5.13 (m, 1H), 3.44-3.29 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.32, 160.09, 139.05, 137.72, 135.22, 135.18, 129.87, 129.45, 128.83, 127.53, 125.62, 123.85, 122.14, 120.43, 120.37, 119.48, 54.20, 37.26, 29.70; HRMS (ESI): calcd for: C19H13ClF3NO3S [M−H]−=426.0184, obsd [M−H]−=426.0180.

Provenance & Evidence