Triphenylphosphine → HCID 70110729, compound

HRID 1279348Notes

Reaction equation

HRID 1279348 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)(O)[CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][OH:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:12]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18427504HCID 18427504, compound

Product 1

HCID 70110729HCID 70110729, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

10.4 g (20.5 mmole) of 4-(t-butyldimethylsilyloxy)-2-(3,4-dichlorophenyl)-1-[N-(t-butoxycarbonyl)-N-(2-hydroxyethyl)amino]-2-butanol [prepared as described in step (b) above] and 8.03 g (30.6 mmole) of triphenylphosphine were dissolved in 180 ml of anhydrous toluene and a solution of 5.33 g (30.6 mmole) of diethyl azodicarboxylate in 20 ml of toluene was added dropwise under a nitrogen atmosphere at room temperature. The mixture was then stirred for 2 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of ammonium chloride and extracted with ethyl acetate. The mixture was then washed with a saturated aqueous solution of sodium chloride. The organic extract was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 23:2 to 9:1 by volume as the eluent, to obtain 8.85 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe mixture was then washed with a saturated aqueous solution of sodium chloride
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washa gradient elution method

Sources & evidence

ORD record
ord-00c9dca3dabf4f3180d271d9bc9b8d65
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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