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

HRID 1167422Notes

Reaction equation

HRID 1167422 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][S:39][N:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[S: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 178516663HCID 178516663, compound

Product 1

HCID 497387(5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isothiazol-3-yloxymethyl)oxazolidin-2-oneYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (227 mg, 1.12 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 (300 mg, 1.02 mmol ; see Example 1), 3-hydroxyisothiazole (114 mg, 1.13 mmol) and triphenylphosphine (304 mg, 1.16 mmol) in THF (8.0 ml). The resulting solution was stirred at room temperature for 30 minutes before evaporating the solvent to give an orange oil. It was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (3:2)) to give the title product (257 mg, 67%) as a colourless crystalline solid. MS: ESP+ (M+H)+=377.

Workup

  1. custombefore evaporating the solvent
  2. customto give an orange oil
  3. customIt was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (3:2))

Sources & evidence

ORD record
ord-f9d5f05f4d4d4fe7b204bb5aa1b4530e
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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