Réaction #42374

Équation de réaction

N,N-diisopropylethylamine

4-(1,3-oxazol-2-yl)benzoic acid

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride

HATU

→

title compound

N-{(1S,2R)-1-(3,5-Difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-4-(1,3-oxazol-2-yl)benzamide

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture is partitioned between methylene chloride and water
2. 2
   LavageThe organic layer is washed with water
3. 3
   Séchagedried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   Autreto afford a crude solid
7. 7
   AutrePurification by flash column chromatography (silica, gradient 96:4 to 93:7 methylene chloride/methanol)

Mode opératoire

To a solution of 4-(1,3-oxazol-2-yl)benzoic acid (105 mg, 0.6 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride (220 mg, 0.6 mmol), and HATU (210 mg, 0.6 mmol) stirring in methylene chloride (5 mL) is added N,N-diisopropylethylamine (340 μL, 1.9 mmol). The reaction mixture is stirred at room temperature for 18 h. The reaction mixture is partitioned between methylene chloride and water. The organic layer is washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a crude solid. Purification by flash column chromatography (silica, gradient 96:4 to 93:7 methylene chloride/methanol) provided the title compound. ESI MS m/z 506.2 [M+H]+.

Source