3-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride → (R)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid

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Reaction Steps

Following the 9a synthetic method, using 3-chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride (249.09 mg, 1.0 mmol) instead of 3 gave 7a as a colorless oil; (145.32 mg, 36.9%). [α]D25: +18.3 (c=0.37, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.97-7.87 (m, 2H), 7.73 (d, J=6.6 Hz, 1H), 7.45-7.38 (m, 1H), 7.18-7.15 (m, 2H), 6.80-6.77 (m, 2H), 4.96-4.90 (m, 1H), 3.34-3.16 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.56, 163.89, 160.62, 159.45, 156.42, 139.16, 133.55, 130.54, 127.03, 124.94, 118.51, 115.22, 114.80, 109.29, 108.95, 54.14, 35.98; HRMS (ESI): calcd for: C18H13ClFNO4S [M−H]−=392.0165, obsd [M−H]−=392.0174.

Provenance & Evidence