Reaktion #1015400

Reaktionsgleichung

HATU

Hunig's Base

1-amino-1-cyclopropanecarbonitrile hydrochloride

H-Boc

HCl

(S)-3-(4-(allyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoic acid

→

[(S)-2-(4-Allyloxy-phenyl)-1-(1-cyano-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with AcOEt (3×75 mL)
2. 2
   TrocknenThe organic layers were dried over Na2SO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe crude material was dissolved in CH2Cl2 (10 mL), 2 minutes later it
5. 5
   Sonstigeto precipitate
6. 6
   FiltrationThe suspension was filtered
7. 7
   SonstigeThe filtered solution was purified by flash chromatography (silica gel, 80 g, 0% to 90% AcOEt in heptane)
8. 8
   Sonstigeto yield a light yellow solid (3.0 g; 50%)

Vorschrift

(S)-3-(4-(allyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoic acid (5 g, 15.6 mmol, Eq: 1.00) was dissolved in DMF (30 ml). HATU (11.8 g, 31.1 mmol, Eq: 2.00), Hunig's Base (4.02 g, 5.43 ml, 31.1 mmol, Eq: 2.00) and 1-amino-1-cyclopropanecarbonitrile hydrochloride (2.21 g, 18.7 mmol, Eq: 1.20) were added to the above suspension and stirred at 25° C. for 24 h. The reaction mixture was poured into 0.1M HCl (250 mL) and extracted with AcOEt (3×75 mL). The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in CH2Cl2 (10 mL), 2 minutes later it began to precipitate. The suspension was filtered. The filtered solution was purified by flash chromatography (silica gel, 80 g, 0% to 90% AcOEt in heptane) to yield a light yellow solid (3.0 g; 50%). m/z=286.1 [M+H-Boc]+.

Quelle