Oxygen difluoride → Oxygen difluoride

HRID 275523

Reaction equation

HRID 275523 reaction equation
[CH3:1][C:2]([O:4][F:5])=[O:3].C(O)[C@H]1O[C@H](O)[C@H]([18F])[C@@H](O)[C@@H]1O.[O:18]([F:20])[F:19].[CH2:21]([O:23][C:24](=[O:56])[C@H:25]([CH2:29][C:30]1[C:35]([Sn](C)(C)C)=[CH:34][C:33]([O:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[C:32]([O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH:31]=1)[NH:26][CH:27]=[O:28])[CH3:22]>C(Cl)(Cl)(Cl)F.C(Cl)Cl>[CH2:21]([O:23][C:24](=[O:56])[C@H:25]([CH2:29][C:30]1[C:35]([F:5])=[CH:34][C:33]([O:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[C:32]([O:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH:31]=1)[NH:26][CH:27]=[O:28])[CH3:22].[CH3:1][C:2]([O:4][F:5])=[O:3].[O:18]([F:20])[F:19]

Participants

9

Reactant 4

HCID 24547Oxygen difluorideHCID 127602Acetyl hypofluoriteHCID 450503alpha-D-Glucopyranose, 2-deoxy-2-(fluoro-18F)-HCID 11828229N-Formyl-3,4-di-t-butoxycarbonyloxy-6-(trimethylstannyl)-L-phenylalanine ethyl ester

Product 3

HCID 24547Oxygen difluorideHCID 127602Acetyl hypofluoriteHCID 15345888N-Formyl-3,4-di-t-butoxycarbonyloxy-6-fluoro-L-phenylalanine ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6389TrichlorofluoromethaneSolvent

Procedure

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).

Workup

  1. washthe organic phase was washed with 1M Na2S2O5 (2×20 mL), water (2×20 mL)
  2. dry with materialdried (MgSO4)
  3. customEvaporation of solvents
  4. customgave a yellow syrup which
  5. customwas chromatographed (silica gel, diethyl ether)

Sources & evidence

ORD record
ord-7a49c58bbbd24d8bb548a600f68ed707
Source dataset
uspto-grants-1995_02
Patent number
US05393908

Linked notes

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