Reaktion #536656

Reaktionsgleichung

Isopropyl iodide

methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate

potassium carbonate

→

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate

Ausbeute 98.8%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was partitioned between water and ethyl acetate
2. 2
   WaschenThe organic phase was washed with saturated brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

Isopropyl iodide (680 uL, 6.8 mmol) was added to a mixture of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (1 g, 3 mmol) (Step 1) and potassium carbonate (940 mg, 6.8 mmol) in acetonitrile (20 mL). The reaction was heated at 60° C. overnight. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-isopropoxyphenyl)propanoate (1 g, 90%) as a white solid. Analytical LCMS (M+H-Boc)+: m/z=237.9.

Quelle