2-Amino-1-butanol, (+)- → (S)-N-(1-hydroxybutan-2-yl)-2-(3'-(methoxymethyl)biphenyl-4-yl)-2-methylpropanamide

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Reaction Steps

Prepared in a similar manner to Example 27 from 2-(3′-(methoxymethyl)biphenyl-4-yl)-2-methylpropanoic acid (example 39a) and (S)-2-aminobutan-1-ol. Yield: 52%. 1H NMR (DMSO-d6, 400 MHz) δ 7.61 (m, 4H), 7.44 (m, 3H), 7.31 (d, 1H, J=7.2 Hz), 6.83 (d, 1H, J=8.5 Hz), 4.57 (t, 1H, J=5.8 Hz), 4.84 (s, 2H), 3.68 (m, 1H), 3.34 (m, 1H), 3.33 (s, 3H), 3.22 (m, 1H), 1.56 (m, 1H), 1.49 (s, 6H), 1.29 (m, 1H), 0.76 (t, 3H, J=7.3 Hz). 13C NMR (DMSO-d6, 100 MHz) δ 175.5, 145.8, 139.8, 139.2, 137.8, 128.9, 126.5, 126.5, 126.4, 125.6, 125.6, 73.6, 63.0, 57.6, 52.5, 46.1, 27.1, 27.0, 23.5, 10.6. M+H=356, m.p.=73-75° C.

Provenance & Evidence