Reaktion #1715517

Reaktionsgleichung

tert-butyl (S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

Tert-butyl (S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

hydrogen chloride

→

101.1.B

Ausbeute 87.2%

(S)-2-Amino-N-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-yl)-3-phenylpropanamide

Ausbeute 87.2%

Lösungsmittel

1,4-dioxane

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed by rotary evaporation
2. 2
   Waschenwashed successively with saturated sodium bicarbonate, water and brine
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated in vacuo

Vorschrift

To a 25 ml flask was added tert-butyl (S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 101.1.A (568 mg, 1.30 mmole), 5 ml of 4N-hydrogen chloride solution in 1,4-dioxane, and 5 ml of 1,4-dioxane. The reaction was stirred at room temperature for 0.5 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo to give 101.1.B (380 mg, 87% yield) as colorless syrup. 1H NMR (400 MHz, CDCl3) δ ppm 9.71 (s, 1H), 8.61 (d, J=5.8 Hz, 2H), 7.69 (d, J=6.2 Hz, 2H), 7.39-7.26 (m, 5H), 6.88 (s, 1H), 4.07 (q, J=7.2 Hz, 2H), 3.85 (dd, J=8.8, 4.1 Hz, 1H), 3.36 (dd, J=13.8, 4.1 Hz, 1H), 2.93 (dd, J=13.9, 8.8 Hz, 1H), 2.96 (brs, 2H), 1.45 (t, J=7.2 Hz, 3H).

Quelle