Triphenylphosphine → HCID 59409859, compound

HRID 2066819Notes

Reaction equation

HRID 2066819 reaction equation
[N:1]([CH2:4][C:5]1([CH3:18])[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][CH2:4][C:5]1([CH3:18])[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 59409876HCID 59409876, compound2×

Product 1

HCID 59409859HCID 59409859, compoundYield 88,800.102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(azidomethyl)-3-(5-chloropyridin-2-yl)-5-methyl-1,3-oxazolidin-2-one (570 mg, INTERMEDIATE 18) and triphenylphosphine (1.12 g) was heated to 65° C. for 4 h in 80 ml of tetrahydrofuran and 10 ml of water. The sample was then cooled to room temperature, and concentrated in vacuo. The residue was purified via column chromatography on a Biotage Horizon 40M column eluting with 100% ethyl acetate (4 column volumes) to remove excess triphenylphosphine and triphenylphosphine oxide, followed by 100% methanol (4 column volumes), to provide the title compound (457 g, 89%). Mass spectrum (ESI) 242.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via column chromatography on a Biotage Horizon 40M column
  3. washeluting with 100% ethyl acetate (4 column volumes)
  4. customto remove excess triphenylphosphine and triphenylphosphine oxide

Sources & evidence

ORD record
ord-4104da69f9c742d4bec90ef4cc5f63bd
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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