Reaktion #42296

Reaktionsgleichung

3-[butyryl(propyl)amino]-5-methylbenzoic acid

3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid

(2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol trifluoroacetate

triethylamine

dichloromethane

diethyl cyanophosphonate

→

title compound

N-{(1S,2R)-1-Benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-[butyryl(propyl)amino]-5-methylbenzamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDichloromethane is then removed under reduced pressure
2. 2
   SonstigeThe residue is partitioned between ethyl acetate and water
3. 3
   SonstigeThe organic is separated
4. 4
   Waschenis washed with saline
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigechromatographed (silica gel; methanol/dichloromethane, 5/95)

Vorschrift

Following the procedure of Example 570 and making non-critical variations, diethyl cyanophosphonate (0.0760 mL, 0.550 mmol) is added to a mixture of 3-[butyryl(propyl)amino]-5-methylbenzoic acid (IX, 0.120 g, 0.460 mmol), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, 0.137 g, 0.460 mmol), and triethylamine (0.0760 mL, 0.550 mmol) in dichloromethane (5 mL). The mixture is stirred for 1 hour at 20-25 degrees C. Dichloromethane is then removed under reduced pressure. The residue is partitioned between ethyl acetate and water. The organic is separated, is washed with saline, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate is column chromatographed (silica gel; methanol/dichloromethane, 5/95) to give the title compound, NMR (400 MHz, CDCl3) δ 7.09, 4.15, 3.80, 3.79, 3.60, 3.02, 2.84, 2.36, 1.94, 1.56, 1.49, 0.87 and 0.81;. MS (ESI+) for C33H43N3O4 m/z (M+H)+=546.3; HRMS (FAB) calculated for C33H43N3O4+H=546.3331, found=546.3331.

Quelle