(S)-methyl 2-hydroxy-3-phenylpropanoate → (R)-2-[4-(Benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy]-3-phenyl-propionic acid

Participants

Reaction Steps

Prepared from 4-benzo[b]naphtho[2,3-d]thiophen-11-yl-phenol (Example 14) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: [a]25/D =-19.09° (8.538 mg/mL, CHCl3); NMR (CDCl3); δ8.30 (s, 1 H), 7.91 (d, J=8 Hz, 1 H), 7.73 (d, J=8 Hz, 1 H), 7.55-7.24 (m, 10 H), 7.14-7.09 (m, 2 H), 7.05 (ddd, J =8, 7, 1 Hz, 1 H), 6.70 (d, J=8 Hz, 1 H), 5.09 (dd, J=8,5 Hz, 1 H,), 3.42 (m, 2 H); MS (EI): [M+] 474 (100%); Anal Calc. for C31H22O3S: C, 78.46, H, 4.67, N, 0.00. Found: C, 77.09, H, 4.60, N, 0.03 Analytical HPLC purity (98.5%).

Provenance & Evidence