Réaction #42371

Équation de réaction

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

diisopropylethylamine

3-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acid

HATU

→

title compound

Methyl 3-(2-{3-[({(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}amino)carbonyl]phenyl}-1,3-oxazol-5-yl)propanoate

Solvants

DMF

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONare added
2. 2
   AutreThe reaction is partitioned between ethyl acetate and saturated sodium bicarbonate
3. 3
   LavageThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
4. 4
   Séchagedried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutrePurification by flash column chromatography (silica, 8% methanol/chloroform)

Mode opératoire

3-[5-(3-Methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoic acid (285 mg, 1.0 mmol) is dissolved in methylene chloride (5 mL) and DMF (5 mL), and diisopropylethylamine (695 μL, 4.0 mmol), HATU (472 g, 1.2 mmol), and (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol dihydrochloride prepared by the method of Example SP-272 (448 mg, 1.1 mmol) are added. The reaction stirred at room temperature 1 h. The reaction is partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) provides the title compound. ESI MS m/z 591.9 [M+H]+.

Source