Triphenylphosphine → HCID 57126803, compound

HRID 1167454Notes

Reaction equation

HRID 1167454 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][OH:23])[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O[C:27]1[CH:31]=[CH:30][O:29][N:28]=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.CCOC(C)=O>[O:1]1[C:5]2([CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][O:23][C:27]5[CH:31]=[CH:30][O:29][N:28]=5)[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21356569HCID 21356569, compoundHCID 178516613HCID 178516613, compound

Product 1

HCID 57126803HCID 57126803, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-(1,4-Dioxa-8-azaspiro[4,5]decan-8-yl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (3.52 g, 10 mmol), 3-hydroxyisoxazole (893 mg, 10.05 mmol), and triphenylphosphine (3.03 g, 12 mmol) were dissolved by stirring in dry tetrahydrofuran (75 ml) under nitrogen. The mixture was cooled in an ice-bath, and diisopropylazodicarboxylate (2.33 g, 12 mmol) added dropwise over 10 minutes. The solution was stirred 18 hours, allowing the temperature to rise to ambient. The mixture was diluted with EtOAc (750 ml). the organic layer washed with water (3×500 ml), dried (magnesium sulfate) and evaporated. The residue was purified by MPLC on silica, eluting with a gradient between 0.25% and 1% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give product (3.58 g).

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. washthe organic layer washed with water (3×500 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by MPLC on silica
  6. washeluting with a gradient between 0.25% and 1% MeOH in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-02b4cd7e47ad49d9897b5dbff728206e
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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