3-Chloro-6-fluorobenzo[b]thiophene-2-carboxylic acid → N-[(3-Chloro-6-fluorobenzo[b]thien-2-yl)carbonyl]-D-phenylalanine

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Reaction Steps

Following the 2a synthetic method, using 3-chloro-6-fluorobenzo[b]thiophene-2-carboxylic acid (115.32 mg, 0.5 mmol) instead of 3-chloro-6-methylbenzo[b]thiophene-2-carboxylic acid gave 4a as a white powder; (177.01 mg, 93.7%). [α]D25: −21.9 (c=0.37, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.95-7.76 (m, 3H), 7.44-7.22 (m, 6H), 5.04-4.97 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.48, 163.90, 160.62, 159.50, 139.15, 136.67, 133.50, 129.50, 128.40, 126.89, 124.94, 118.57, 115.15, 114.82, 109.30, 108.95, 53.95, 36.78; HRMS (ESI): calcd for: C18H13ClFNO3S [M+H]+=378.0361, obsd [M+H]+=378.0347.

Provenance & Evidence