N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine → (2S)-2-(2-Fluorobenzenesulfonamido)-3-phenylpropanoic acid

Participants

Reaction Steps

Following the 14a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 14b as a colorless oil; (102.01 mg, 63.1%). [α]D25: +16.3 (c=0.39, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.82 (dd, J=1.8, 7.8 Hz, 1H), 7.59-7.52 (m, 1H), 7.26-7.21 (m, 4H), 7.15-7.08 (m, 3H), 5.27 (d, J=9 Hz, 1H), 4.43 (m, 1H), 3.20-3.05 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.53, 160.51, 157.15, 136.55, 134.91, 134.79, 129.48, 129.31, 128.18, 126.68, 124.15, 117.04, 116.75, 57.32, 38.37; HRMS (ESI): calcd for C15H14FNO4S: [M+Na]+=346.0508, obsd [M+Na]+=324.0520.

Provenance & Evidence