Reacción #42345

Ecuación de reacción

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

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

diisopropylethylamine

HATU

→

title compound

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is partitioned between chloroform and water
2. 2
   LavadoThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
3. 3
   Secadodried (sodium sulfate)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroPurification by flash column chromatography (silica, 8% methanol/chloroform)

Procedimiento

To 3-{[methyl(propyl)amino]carbonyl}-5-(1,3-oxazol-2-yl)benzoic acid (206 mg, 0.71 mmol) in DMF (5 mL) is added diisopropylethylamine (174 μL, 1.1 mmol), HATU (323 mg, 0.85 mmol), then (2R,3S)-3-amino-1-[(3-ethylbenzyl)amino]-4-phenylbutan-2-ol dihydrochloride prepared by the method of Example SP-272 (292 mg, 0.79 mmol). The reaction is stirred 4 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 brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) gives the title compound. ESI MS m/z 569.3 [M+H]+.

Fuente