Reaktion #89578

Reaktionsgleichung

benzyl chloride

Boc-Phe-OH

potassium carbonate

→

title compound

Ausbeute 95.8%

benzyl (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoate

Ausbeute 95.8%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (75 mL, 2×25 mL)
2. 2
   WaschenThe combined organics were washed with brine (200 mL), water (3×100 mL) and brine (50 mL)
3. 3
   TrocknenThe organic phase was dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigethen chromatographed on silica gel eluting with 0%-20% ethyl acetate in hexanes
7. 7
   EinengenThe product-containing fractions were concentrated in vacuo

Vorschrift

To a stirred solution of Boc-Phe-OH (10 g, 37.7 mmoL) in DMF (50 mL) was added potassium carbonate (7.81 g, 56.5 mmol) followed by benzyl chloride (4.55 mL, 39.6 mmol) and the resulting suspension was stirred at 60° C. for 3 d. The mixture was diluted with water (400 mL) and extracted with ethyl acetate (75 mL, 2×25 mL). The combined organics were washed with brine (200 mL), water (3×100 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated then chromatographed on silica gel eluting with 0%-20% ethyl acetate in hexanes. The product-containing fractions were concentrated in vacuo giving the title compound (12.84 g, 95%) as a white solid.

Quelle