4-Fluorobenzenesulfonyl chloride → (R)-2-(4-fluoro-benzenesulfonylamino)-3-phenyl-propionic acid

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Reaction Steps

Following the 14a synthetic method, using 4-fluorobenzenesulfonyl chloride (97.31 mg, 0.5 mmol) instead of 2-fluorobenzenesulfonyl chloride gave 16a as a colorless oil; (108.48 mg, 67.1%). [α]D25: −19.1 (c=0.41, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.77-7.73 (m, 2H), 7.24-7.21 (m, 7H), 6.92 (d, J=9 Hz, 1H), 4.21-4.14 (m, 1H), 3.15-2.90 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.55, 166.28, 162.95, 137.53, 136.53, 129.74, 129.62, 129.39, 128.24, 126.68, 115.93, 115.63, 57.29, 38.49; HRMS (ESI): calcd for: C15H14FNO4S [M+Na]+=346.0520, obsd [M+Na]+=346.0513.

Provenance & Evidence