Reaktion #86642

Reaktionsgleichung

N-BOC-tyrosine methyl ester

potassium carbonate

4-bromo-1-butene

→

(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

Lösungsmittel

EtOAc

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned with 1M hydrochloric acid
2. 2
   WaschenThe organic phase was washed with hydrochloric acid
3. 3
   Trocknenwith brine before being dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
7. 7
   Sonstigeto yield a white solid, 3.20 g, 27%

Vorschrift

N-BOC-tyrosine methyl ester (10.0 g, 33.9 mmol) was dissolved in DMF (40 mL) and potassium carbonate (5.62 g, 40.7 mmol) and 4-bromo-1-butene (4.13 mL, 40.7 mmol) were added. The mixture was stirred at rt for 18 h before being diluted with EtOAc (120 mL) and partitioned with 1M hydrochloric acid. The organic phase was washed with hydrochloric acid and then with brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 3.20 g, 27%. Rf=0.82 (1/2 EtOAc/(50/70) petroleum ether).

Quelle