6-Fluoro-1-benzothiophene-2-carboxylic acid → (R)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

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Reaction Steps

Following the 2a synthetic method, using 8-1-acid (98.10 mg, 0.5 mmol) instead of 3-chloro-6-methylbenzo[b]thiophene-2-carboxylic acid gave 13a as a colorless oil (159.84 mg, 93.1%). [α]D25: −21.1 (c=0.33, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.03 (d, J=8.1 Hz, 1H), 7.98 (s, 1H), 7.90-7.86 (m, 1H), 7.75-7.71 (m, 1H), 7.34-7.13 (m, 6H), 4.95-4.87 (m, 1H), 3.36-3.10 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 172.09, 163.11, 161.49, 159.87, 142.28, 139.46, 137.49, 136.19, 129.22, 128.33, 126.89, 126.63, 126.61, 124.44, 114.09, 108.67, 54.08, 37.01; HRMS (ESI): calcd for: C18H14FNO3S [M−H]−=342.0606, obsd [M−H]−=342.0594.

Provenance & Evidence