Reaktion #1715408

Reaktionsgleichung

2-(benzyloxy)-5-bromobenzenamine

2-(Benzyloxy)-5-(pyridin-4-yl)benzenamine

(S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid

diisopropylethylamine

2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium hexafluorophosphate

DMF

→

tert-butyl (S)-1-(3-(1H-pyrazol-4-yl)phenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

Ausbeute 35.0%

(S)-tert-butyl 1-(2-(benzyloxy)-5-(pyridin-4-yl)phenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

Ausbeute 35.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was then partitioned between water and EtOAc
2. 2
   Sonstigethe organic layer was separated
3. 3
   Extraktionthe aqueous phase was extracted with additional EtOAc
4. 4
   WaschenThe combined organic layers were washed with water and brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by silica gel flash chromatography (0-100% EtOAc/hexane)

Vorschrift

To a solution of 2-(benzyloxy)-5-bromobenzenamine 13.D (1.59 g, 5.76 mmol) in DMF (20 mL) was added (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (1.83 g, 6.91 mmol, available from Aldrich), diisopropylethylamine (1.50 mL, 8.64 mmol) and 2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium hexafluorophosphate (2.62 g, 6.91 mmol). The resulting mixture is stirred overnight at room temperature. The mixture was then partitioned between water and EtOAc, the organic layer was separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-100% EtOAc/hexane) to afford tert-butyl (S)-1-(3-(1H-pyrazol-4-yl)phenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 13.E (1.25 g, 35% yield).

Quelle