Reaction #640598

Reaction equation

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

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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).

Source