反应详情

(S)-N-Isoleucyl-4-allyloxybenzamide isopropyl ester was prepared as in Example 1 except 2.6 g (0.015 mole) of 4-allyloxybenzoic acid and 2.5 g (0.014 mole) of (S)-isopropyl isoleucinate were used in Example 2 rather than the 2.0 g of 4-allyloxybenzoic acid and 2 g (S)-1-(1-naphthyl)ethylamine in Example 1. The product was recrystallized twice from petroleum ether (30°-60°) to give 2.1 g (37%) of (S)-N-isoleucyl-4-allyloxybenzamide isopropyl ester as a white crystalline solid; mp 48°-48.5° C.; [α]D25 +48.93° (c=0.329, CHCl3); IR (KBr): 3300, 1725 and 1625 cm-1 ; NMR (δ): 0.96-1.12 (6H, m), 1.36 (6H, d, J=7.2 Hz), 1.40-1.76 (2H, m), (1H, broad, signal disappeared in D2O), 1.96-2.16 (1H, m,), 4.46 (2H, d, J=6.3 Hz), 4.74-5.20 (2H, m) 5.24-5.56 (2H, m) 5.88-6.28 (1H, m) 6.96 (2H, d, J=8.5 Hz), 7.80 (2H, d, J=8.5 Hz). Anal. for C19H27NO4 : Calcd: C, 68.47; H, 8.11; N, 4.20. Found: C, 68.50: H, 8.00; N, 4.30.

1. customThe product was recrystallized twice from petroleum ether (30°-60°)