反应 #42358

反应方程式

Methyl hydrogen isophthalate

2-amino-4-(benzyloxy)butan-1-ol hydrochloride

diisopropylethylamine

HATU

→

title compound

Methyl 3-({[3-(benzyloxy)-1-(hydroxymethyl)propyl]amino}carbonyl)benzoate

溶剂

ethyl acetate

DMF

反应条件

后处理

1. 1
   洗涤washed with water, 1N hydrochloric acid (aq), saturated sodium bicarbonate, brine
2. 2
   干燥dried (magnesium sulfate)
3. 3
   过滤filtered
4. 4
   浓缩concentrated under reduced pressure
5. 5
   其他Purification by flash column chromatography (silica gel, 4% methanol/chloroform)

实验过程

Methyl hydrogen isophthalate (1.5 g, 8.2 mmol), 2-amino-4-(benzyloxy)butan-1-ol hydrochloride (2 g, 8.6 mmol), diisopropylethylamine (4.2 mL, 24.7 mmol), and HATU (3.8 mg, 9.9 mmol), in DMF (15 mL) are stirred at room temperature 1 h. The reaction is diluted in ethyl acetate and washed with water, 1N hydrochloric acid (aq), saturated sodium bicarbonate, brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 4% methanol/chloroform) provides the title compound. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.18 (d, 1H, J=7.9 Hz), 7.86 (d, 1H, J=7.9 Hz), 7.43 (t, 1H, J=7.6 Hz), 7.42-7.35 (m, 5H), 4.59 (s, 2H), 4.33 (m, 1H), 3.96 (s, 3H), 3.88-3.72 (m, 4H), 3.53 (s, 1H), 2.08 (m, 2H).

来源