Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167416Notes

Reaction equation

HRID 1167416 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH2:30][CH2:31][O:32][CH2:33][CH:34]=3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1.O[C:37]1[CH:41]=[CH:40][O:39][N:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:39]1[CH:40]=[CH:41][C:37]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH2:30][CH2:31][O:32][CH2:33][CH:34]=4)=[C:25]([F:35])[CH:24]=3)[CH2:18]2)=[N:38]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 186848415(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 497377(5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isoxazol-3-yloxymethyl)oxazolidin-2-oneYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (248 mg, 1.22 mmol) was added dropwise, at ambient temperature, to a stirred solution of 5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (International Patent Application Publication WO 97/09328) (300 mg, 1.02 mmol), 3-hydroxyisoxazole (104 mg, 1.22 mmol) and triphenylphosphine (340 mg, 1.30 mmol) in THF (8.0 ml). The resulting solution was stirred at ambient temperature for 30 minutes before evaporating the solvent to give an oil which was purified by flash chromatography (Merck 9385 silica, EtOAc/iso-hexane (7:3) eluant) to give the title product (219 mg, 59%) as a crystalline solid.

Workup

  1. custombefore evaporating the solvent
  2. customto give an oil which
  3. customwas purified by flash chromatography (Merck 9385 silica, EtOAc/iso-hexane (7:3) eluant)

Sources & evidence

ORD record
ord-a0e444de6ee64bacbc7c5acbba5dfec9
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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