Reacción #42468

Ecuación de reacción

4-Butyl-8-(1,3-oxazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid

HBTU

diisopropylethylamine

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

→

title compound

4-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-8-(1,3-oxazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxamide

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered with methylene chloride
2. 2
   Secadodried (magnesium sulfate)
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroPurification by flash column chromatography (silica, 1:9 methanol/chloroform)

Procedimiento

A solution of 4-Butyl-8-(1,3-oxazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid (450 mg, HBTU (853 mg), and diisopropylethylamine (580 mg) was stirred in methylene chloride (15 mL) for 15 min. A solution of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (606 mg) in methylene chloride (7 mL) was added and the reaction mixture was stirred overnight. The mixture was filtered with methylene chloride, dried (magnesium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 methanol/chloroform) provided 400 mg of the title compound: ESI MS m/z 619 [M+H]+.

Fuente