Reacción #362705

Ecuación de reacción

CH3COOF

2-[18F]fluoro-2-deoxy-D-glucose

OF2

trimethyltin

N-Formyl-3,4-di-t-butoxycarbonyloxy-6-(trimethylstannyl)-L-phenylalanine ethyl ester

→

oil 9

N-Formyl-3,4-di-t-butoxycarbonyloxy-6-fluoro-L-phenylalanine ethyl ester

CH3COOF

OF2

Disolventes

methylene chloride

Freon-11

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic phase was washed with 1M Na2S2O5 (2×20 mL), water (2×20 mL)
2. 2
   Secadodried (MgSO4)
3. 3
   OtroEvaporation of solvents
4. 4
   Otrogave a yellow syrup which
5. 5
   Otrowas chromatographed (silica gel, diethyl ether)

Procedimiento

The electrophilic fluorinating agent, CH3COOF (prepared from 200 μmol) of F2 in 1% He, (Bida, G. T., Satyamurthy, N. and Barrio, J. R. (1984) The synthesis of 2-[18F]fluoro-2-deoxy-D-glucose using glycals: A reexamination. J. Nucl. Med. 25, 1327) F2 (1% in He, 200 μmol) or OF2 (1% in He, 200 μmol), was bubbled into a solution of trimethyltin derivative 6 (0.123 g, 200 μmol) in Freon-11 (CFCl3) (20 mL) at room temperature over a period of 30 min. The reaction mixture was diluted with methylene chloride (25 mL) and the organic phase was washed with 1M Na2S2O5 (2×20 mL), water (2×20 mL) and dried (MgSO4). Evaporation of solvents gave a yellow syrup which was chromatographed (silica gel, diethyl ether) to yield a colorless viscous oil 9 (41 mg, 43% in the case of CH3COOF), (65 mg, 69% for F2), (62 mg, 66% for OF2).

Fuente