Triphenylphosphine → 3-(3-Fluoro-4-iodo-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-one

HRID 1247487Notes

Reaction equation

HRID 1247487 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH:12]([CH2:14][OH:15])[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1[I:8].[O:17]1[CH:21]=[CH:20][C:19](O)=[N:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH:12]([CH2:14][O:15][C:19]3[CH:20]=[CH:21][O:17][N:18]=3)[O:11][C:10]2=[O:16])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 218778583-(3-Fluoro-4-iodo-phenyl)-5-(hydroxymethyl)oxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 219074133-(3-Fluoro-4-iodo-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-oneYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-oxazolidin-2-one (1.0 g, 2.97 mmol), isoxazol-3-ol (0.30 g, 3.56 mmol) and triphenylphosphine (1.02 g, 3.86 mmol) in THF (15 mL) was added diisopropyl azodicarboxylate (DIAD, 0.74 mL, 3.56 mmol) dropwise at 0° C. The reaction was warmed to room temperature and stirring was continued for 2 h. The solvent was evaporated and the crude was purified on silica gel, eluting with hexanes/EtOAc 2:1 to 3:2, to give 3-(3-fluoro-4-iodo-phenyl)-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-one (1.01 g; 84% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was purified on silica gel
  3. washeluting with hexanes/EtOAc 2:1 to 3:2

Sources & evidence

ORD record
ord-9c5c10877d5a454cae6d23e46b2c2f92
Source dataset
uspto-grants-2006_10
Patent number
US07129259B2

Reaction notes

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