(R)-(-)-2-Amino-1-phenylethanol → (R)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(2-hydroxy-2-phenylethyl)isonicotinamide

Participants

Reaction Steps

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (R)-2-amino-1-phenylethanol to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, (R)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(2-hydroxy-2-phenylethyl)isonicotinamide was obtained as a colorless solid in 49% yield: mp 97-99° C.; 1H NMR (300 MHz, CDCl3) δ 8.49 (s, 1H), 8.32 (d, J=5.4 Hz, 1H), 7.65 (br s, 1H), 7.39-7.16 (m, 8H), 7.02-6.96 (m, 2H), 5.00 (d, J=6.9 Hz, 1H), 4.36-4.27 (m, 3H), 4.03-3.87 (m, 3H), 3.46-3.31 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 166.7, 164.0, 160.8, 156.9, 152.6, 148.0, 143.2, 141.9, 131.9, 131.9, 129.9, 129.8, 128.5, 127.8, 125.8, 116.2, 115.9, 115.6, 109.5, 48.1, 47.2, 41.4, 41.0; MS (ES+) m/z 434.7 (M+1).

Provenance & Evidence