Reaktion #360446

Reaktionsgleichung

L-tyrosine ethyl ester hydrochloride

NaHCO3

→

N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester

Ausbeute 180.9%

Lösungsmittel

CH2Cl2 H2O

AcOEt

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer was washed with H2O
2. 2
   Trocknendried (Na2SO4)
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe residue was recrystallized from a mixture of diethyl ether and hexane

Vorschrift

To a mixture of L-tyrosine ethyl ester hydrochloride (55.08 g) and NaHCO3 (22.52 g) in CH2Cl2/H2O (280 ml/280 ml) was added di-tert-butyl bicarbonate (56.82 g) portionwise. The mixture was stirred for 2 hours at room temperature and diluted with AcOEt. The organic layer was washed with H2O, dried (Na2SO4) and evaporated. The residue was recrystallized from a mixture of diethyl ether and hexane to yield N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester (62.71 g). mp. 87-88° C.; MS (APCI) m/z 327 (M+NH4), 310 (M+H).

Quelle