Triphenylphosphine → HCID 21881983, compound

HRID 721978Notes

Reaction equation

HRID 721978 reaction equation
O[CH:2]1[O:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[C:3]1=[O:17].[CH3:18][C:19]([C:22]1[CH:26]=[CH:25][NH:24][N:23]=1)([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH3:18][C:19]([C:22]1[CH:26]=[CH:25][N:24]([CH:2]2[O:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=3)[C:3]2=[O:17])[N:23]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11118371HCID 11118371, compoundHCID 178441177HCID 178441177, compound

Product 1

HCID 21881983HCID 21881983, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-oxazolidinone (1 g, 4.05 mmol) in tetrahydrofuran (20 mL) under nitrogen at ˜0° C., were added 3-(1,1-dimethylethyl)-1H-pyrazole (0.5 g, 4.05 mmol), triphenylphosphine (1.23 g, 4.7 mmol) and diisopropyl azodicarboxylate (0.88 mL, 4.46 mmol). After the addition, the reaction mixture was allowed to warm up slowly to room temperature and stirred at room temperature overnight. The reaction mixture was then concentrated, and the residue was purified by column chromatography (silica gel, ˜20% ethylacetate/80% hexanes) to give a crude product. The crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes) to give the title compound, a compound of this invention, as a white solid (14 mg) melting at 95–98° C.

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue was purified by column chromatography (silica gel, ˜20% ethylacetate/80% hexanes)
  4. customto give a crude product
  5. customThe crude product was further purified by column chromatography (silica gel, ˜20% ethyl acetate/˜80% hexanes)

Sources & evidence

ORD record
ord-f2f7e72324854a89a2bb1204f3ff4805
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Reaction notes

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