Réaction #42574

Équation de réaction

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

3-{[Methyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic acid

diisopropylethylamine

HATU

→

title compound

N1-{(1S,2R) -1-(3,5-Difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-N3-methyl-5-(1,3-oxazol-2-yl)-N3-propylisophthalamide

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction is partitioned between chloroform and water
2. 2
   LavageThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride
3. 3
   Séchagedried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutrePurification by flash column chromatography (silica, 9% methanol/chloroform)

Mode opératoire

To 3-{[Methyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic acid (350 mg, 1.2 mmol) in DMF (5 mL) is added diisopropylethylamine (835 μL, 4.8 mmol), HATU (554 mg, 1.5 mmol), then (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride prepared by the method of Example SP-272 (488 mg, 1.2 mmol). The reaction is stirred for 16 h at room temperature. The reaction is partitioned between chloroform and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 9% methanol/chloroform) gives the title compound. ESI MS m/z 605.3 [M+H]+.

Source