반응 #640598

반응 방정식

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine

t-butyl acetate

sulfuric acid

→

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine t-Butyl ester

용매

dichloromethane

반응 조건

후처리

1. 1
   기타Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL)
2. 2
   세척The organic layer was washed with distilled water
3. 3
   기타evaporated
4. 4
   기타The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol)
5. 5
   기타to yield 0.292 g (77%) as a colorless oil

실험 절차

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with t-butyl acetate (3 mL) and concentrated sulfuric acid (40 μL) in a sealed flask at 0° C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol) to yield 0.292 g (77%) as a colorless oil; 1H NMR (CDCl3) δ 1.44 (s, 9H); 3.68 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 3.87 (dd, J=2.9 Hz, J=9.3 Hz, 1H); 4.22 (t, J=7.1 Hz, 1H); 4.30-4.60 (m, 5H); 5.64-5.67 (m, 1H); 7.25-7.39 (m, 9H); 7.58-7.61 (m, 2H); 7.73-7.76 (m, 2H).

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