Reacción #42358

Ecuación de reacción

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

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water, 1N hydrochloric acid (aq), saturated sodium bicarbonate, brine
2. 2
   Secadodried (magnesium sulfate)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification by flash column chromatography (silica gel, 4% methanol/chloroform)

Procedimiento

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).

Fuente