Reaction #42358

Reaction equation

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

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washwashed with water, 1N hydrochloric acid (aq), saturated sodium bicarbonate, brine
2. 2
   Dryingdried (magnesium sulfate)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherPurification by flash column chromatography (silica gel, 4% methanol/chloroform)

Procedure

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).

Source