Triphenylphosphine → HCID 22288645, compound

HRID 968309Notes

Reaction equation

HRID 968309 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]([CH2:19][CH2:20][CH2:21][OH:22])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1([CH2:28][C:29]2[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=2)[CH:27]=[CH:26][N:25]=[CH:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:23]1([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:22][CH2:21][CH2:20][CH2:19][C:10]3[N:11]=[C:12]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8][CH:9]=3)=[CH:33][CH:34]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 1938221-(4-Hydroxybenzyl)imidazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22288646HCID 22288646, compound

Product 1

HCID 22288645HCID 22288645, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(5,6-Diphenyl-2-pyrazinyl)-1-propanol (950 mg), 4-(1H-imidazolylmethyl)phenol (570 mg), and triphenylphosphine (860 mg) were suspended in anhydrous tetrahydrofuran (30 mL). A 40% solution (1.56 g) of diethyl azodicarboxylate in toluene was added dropwise to the resultant suspension under ice cooling, and the resultant mixture was stirred at room temperature for one hour. Ethyl acetate was added to the mixture, and the ethyl acetate layer was washed sequentially by a 10% aqueous solution of sodium hydroxide, water, and saturated saline. The washed product was dried over sodium sulfate anhydrate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column and crystallized from ether, to thereby yield 500 mg of Compound (1R) of the present invention as colorless crystals (yield 34.0%).

Workup

  1. washthe ethyl acetate layer was washed sequentially by a 10% aqueous solution of sodium hydroxide, water, and saturated saline
  2. dry with materialThe washed product was dried over sodium sulfate anhydrate
  3. customthe residual solvent was removed through distillation under reduced pressure
  4. customThe thus-yielded residue was purified by means of a silica gel column
  5. customcrystallized from ether

Sources & evidence

ORD record
ord-11359773f1484a988ca50eab6b7828b7
Source dataset
uspto-grants-2005_10
Patent number
US06958353B2

Reaction notes

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