Triphenylphosphine → (5R)-3-(3-fluoro-4-morpholino-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167425Notes

Reaction equation

HRID 1167425 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]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:11]([F:21])[CH:10]=2)[CH2:4]1.O[C:23]1[CH:27]=[CH:26][O:25][N:24]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:25]1[CH:26]=[CH:27][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]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[C:11]([F:21])[CH:10]=3)[CH2:4]2)=[N:24]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 10541953(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 497404(5R)-3-(3-fluoro-4-morpholino-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-oneYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared by the general method of Example 1 using as starting material 5(R)-hydroxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one (WO95/07271; 300 mg, 1.01 mmol), 3-hydroxyisoxazole (95 mg, 1.12 mmol), diisopropylazodicarboxylate (225 mg, 1.11 mmol) and triphenylphosphine (305 mg, 1.16 mmol) in THF (5 ml). Purified by flash chromatography (Merck 9385 silica. EtOAc/isohexane (7/3)) to give the title compound (254 mg, 69%) as a colourless solid.

Workup

  1. customPrepared by the general method of Example 1 using
  2. customPurified by flash chromatography (Merck 9385 silica. EtOAc/isohexane (7/3))

Sources & evidence

ORD record
ord-dbb42d52fd3a4ad8af0319650b768db4
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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