Triphenylphosphine → (5R)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167462Notes

Reaction equation

HRID 1167462 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[O:15][C:14]2=[O:20])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.O[C:22]1[CH:26]=[CH:25][O:24][N:23]=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>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][O:19][C:22]3[CH:26]=[CH:25][O:24][N:23]=3)[O:15][C:14]2=[O:20])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 104927643-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-oneHCID 178516613HCID 178516613, compound

Product 1

HCID 497412(5R)-3-(3-fluoro-4-imidazol-1-yl-phenyl)-5-(isoxazol-3-yloxymethyl)oxazolidin-2-oneYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one (WO 96/23788; 280 mg, 1 mmol), 3-hydroxyisoxazole (94 mg, 1.1 mmol), and triphenylphosphine (330 mg, 1.25 mmol) were suspended by stirring in dry tetrahydrofuran (10 ml) under nitrogen at ambient temperature. Diisopropylazodicarboxylate (308 mg, 1.5 mmol) was added dropwise over 10 minutes. The suspension dissolved, and stirring was continued at the same temperature for 2 hours. The mixture was evaporated to dryness, and the residue purified by chromatography on a 20 g silica Mega Bond Elut® columns, eluting with a gradient increasing in polarity from 50 to 100% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the desired product (206 mg). MS (ESP): 345 (MH+) for C16H13FN4O4.

Workup

  1. dissolutionThe suspension dissolved
  2. customThe mixture was evaporated to dryness
  3. customthe residue purified by chromatography on a 20 g silica Mega Bond Elut® columns
  4. washeluting with
  5. temperaturea gradient increasing in polarity from 50 to 100% EtOAc in isohexane
  6. customevaporated

Sources & evidence

ORD record
ord-b3b6251e19af4ef2a1c434e00097a7ce
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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