Реакция #42358

Уравнение реакции

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

Растворители

ethyl acetate

DMF

Условия реакции

Обработка

1. 1
   Промывкаwashed with water, 1N hydrochloric acid (aq), saturated sodium bicarbonate, brine
2. 2
   Сушкаdried (magnesium sulfate)
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеPurification by flash column chromatography (silica gel, 4% methanol/chloroform)

Методика

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).

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