Reaktion #939429

Reaktionsgleichung

Trifluoromethanesulfonic anhydride

Boc-L-tyrosine methyl ester

pyridine

→

(S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl) propionic acid methyl ester

Ausbeute 90.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by addition of NaHCO3 solution (150 ml)
2. 2
   Sonstigethe organic layer was separated
3. 3
   Waschenwashed with saturated aqueous NaHCO3 (2×100 ml) and brine (1×100 ml)
4. 4
   Trocknendried (MgSO4)
5. 5
   EinengenThe solvent was concentrated under reduced pressure

Vorschrift

Trifluoromethanesulfonic anhydride (3.27 ml, 19.47 mmol) was slowly added to a solution of Boc-L-tyrosine methyl ester (5.0 g, 16.93 mmol) and pyridine (4.11 ml, 50.79 mmol) in dichloromethane (145 ml) at 0° C. and the resulting orange solution was stirred at room temperature for 4 h. The reaction was quenched by addition of NaHCO3 solution (150 ml) and the organic layer was separated, washed with saturated aqueous NaHCO3 (2×100 ml) and brine (1×100 ml), and dried (MgSO4). The solvent was concentrated under reduced pressure to yield (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl) propionic acid methyl ester (6.52 g, 90%) that was used in the next step without further purification.

Quelle