Triphenylphosphine → HCID 70023347, compound

HRID 1861660Notes

Reaction equation

HRID 1861660 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][OH:23])[C:10]([NH:12][CH2:13][CH2:14]N2CCCCC2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P([C:37]2[CH:42]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:43]([C:51](OC(C)C)=O)=NC(OC(C)C)=O.[C:57](O)(=S)[CH3:58].C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]1([CH2:7][CH2:8][N:9]([CH2:21][CH2:22][OH:23])[C:10]([NH:12][CH2:13][CH:14]2[CH2:37][CH2:42][N:43]([CH3:51])[CH2:57][CH2:58]2)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 516892Sodium BicarbonateHCID 15541414HCID 15541414, compound2×HCID 178418634HCID 178418634, compound

Product 1

HCID 70023347HCID 70023347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-Cyclohexylethyl)-1-(2-hydroxyethyl)-3-[2-(1-piperidyl) ethyl]urea (Compound 1-1, 0.94 g) and triphenyl phosphine (1.52 g) were dissolved in anhydrous tetrahydrofuran (14 ml) in the nitrogen gas atmosphere and the resulting solution was stirred for 30 minutes under sodium chloride-ice cooling. There were dropwise added, to the cooled solution, in order, diisopropyl azodicarboxylate (1.14 ml) and a solution of thioacetic acid (0.44 g) in anhydrous tetrahydrofuran (1 ml), while maintaining the temperature of the solution to not higher than 5° C. After stirring the solution for one hour, a saturated aqueous solution of sodium hydrogen carbonate (40 ml) was added to the reaction solution and then the mixture was extracted with ether. The resulting organic phase was washed with saturated aqueous sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to thus give the title compound (Compound 3-1).

Workup

  1. stirringAfter stirring the solution for one hour
  2. extractionthe mixture was extracted with ether
  3. washThe resulting organic phase was washed with saturated aqueous sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-2ebf90a980d343809f2ec04056983c47
Source dataset
uspto-grants-2003_03
Patent number
US06534499B2

Reaction notes

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