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

HRID 1167417Notes

Reaction equation

HRID 1167417 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:16][CH2:17][O:18][CH2:19][CH:20]=3)=[C:11]([F:21])[CH:10]=2)[CH2:4]1.O[C:23]1[CH:27]=[C:26]([CH3:28])[O:25][N:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:28][C:26]1[O:25][N:24]=[C:23]([O:1][CH2:2][C@@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH2:16][CH2:17][O:18][CH2:19][CH:20]=4)=[C:11]([F:21])[CH:10]=3)[CH2:4]2)[CH:27]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 24781HymexazolHCID 5363146Diisopropyl azodicarboxylateHCID 186848415(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one

Product 1

HCID 497378(5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-[(5-methylisoxazol-3-yl)oxymethyl]oxazolidin-2-oneYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (300 mg, 1.02 mmol), 3-hydroxy-5-methylisoxazole (120 mg, 1.21 mmol), triphenylphosphine (270 mg, 1.03 mmol) and diisopropylazodicarboxylate (204 mg, 1.01 mmol) were reacted in THF (8.0 ml) using the general method of Example 1. The resultant product was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (7:3) eluant) to give the title product (176 mg, 46%) as a crystalline solid.

Workup

  1. customThe resultant product was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (7:3) eluant)

Sources & evidence

ORD record
ord-9759d8846940478da0863aa0df55681e
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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