Triphenylphosphine → HCID 57045614, compound

HRID 1167432Notes

Reaction equation

HRID 1167432 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][OH:26])[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:30]1[CH:34]=[CH:33][O:32][N:31]=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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][C:30]4[CH:34]=[CH:33][O:32][N:31]=4)[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 16203632(r)-Tert-butyl 4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylateHCID 178516613HCID 178516613, compound

Product 1

HCID 57045614HCID 57045614, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-(4-t-Butoxycarbonyl-piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (WO 93/23384; 10 g, 25.3 mmol), 3-hydroxyisoxazole (2.58 g, 30 mmol), and triphenylphosphine (9.95 g, 37.8 mmol) were dissolved in anhydrous tetrahydrofuran (300 ml), and cooled under nitrogen to 4°. Diisopropylazodicarboxylate (6.04 g, 30 mmol) was added dropwise over 10 minutes, and stirring was continued at the same temperature for 2 hours. The mixture was evaporated to dryness, and the residue purified by flash chromatography on silica, eluting with 50% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the desired product (10.2 g).

Workup

  1. temperaturecooled under nitrogen to 4°
  2. customThe mixture was evaporated to dryness
  3. customthe residue purified by flash chromatography on silica
  4. washeluting with 50% EtOAc in isohexane
  5. customevaporated

Sources & evidence

ORD record
ord-5e1c83f4de954cbb9f69353147b29cd7
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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