Reaktion #67545

Reaktionsgleichung

HCl

L-tyrosine O-t-butyl ester

NaHCO3

9-fluorenylmethyl-N-succinimidyl carbonate

→

solid 83

Ausbeute 114.2%

N-(9-fluorenylmethoxycarbonyl)-L-tyrosine

Ausbeute 114.2%

Lösungsmittel

1,4-dioxane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe product was extracted with ethyl acetate (3×)
2. 2
   WaschenThe organic extracts were washed with H2O and saturated aqueous NaCl
3. 3
   Trocknenthen dried over Na2SO4
4. 4
   EinengenThe solution was then concentrated
5. 5
   Filtrationafter filtration

Vorschrift

To a stirring suspension of L-tyrosine O-t-butyl ester (1.00 g, 4.21 mmol) and NaHCO3 (354 mg, 4.21 mmol) in 1,4-dioxane/water (1:1, 20 mL) was added 9-fluorenylmethyl-N-succinimidyl carbonate (1.42 g, 4.21 mmol) and the resulting mixture was stirred for 18 hr at room temperature. The solvent was reduced to 10 mL followed by the addition of 50 mL of cold 1N HCl. The product was extracted with ethyl acetate (3×). The organic extracts were washed with H2O and saturated aqueous NaCl then dried over Na2SO4. The solution was then concentrated after filtration to give the colourless solid 83 (1.94 g, 100%) which was used without purification: 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 2.97-3.06 (m, 2H), 4.21 (bt, J=7.1, 1H), 4.33 (dd, J=7.1, 10.5, 1H), 4.41-4.53 (m, 2H), 5.01 (bs, 1H), 5.30, (d, J=8.2, 1H), 6.73 (d, J=8.5, 2H), 7.00 (d, J=8.5, 2H), 7.31 (t, J=7.5, 2H), 7.40 (t, J=7.5, 2H), 7.57 (dd, J=3.3, 7.3, 2H), 7.76 (d, J=7.5, 2H).

Quelle