Triphenylphosphine → HCID 23446436, compound

HRID 1841625Notes

Reaction equation

HRID 1841625 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]([CH2:18][CH2:19]O)[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.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.[C:54]([OH:57])(=[S:56])[CH3:55].C(=O)([O-])O.[Na+]>O1CCCC1>[C:54]([S:56][CH2:19][CH2:18][N:9]([CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:10]([NH:12][CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])=[O:11])(=[O:57])[CH3:55]

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 516892Sodium BicarbonateHCID 12096929HCID 12096929, compound2×HCID 178418634HCID 178418634, compound

Product 1

HCID 23446436HCID 23446436, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

1-(2-Cyclohexyl ethyl)-3-[2-(dimethylamino)ethyl]-1-(2-hydroxyethyl)-urea (Compound 1-1, 0.57 g) and triphenyl phosphine (1.04 g) were dissolved in anhydrous tetrahydrofuran (10 ml) in the nitrogen gas atmosphere and the resulting solution was stirred under cooling with sodium chloride-ice for 30 minutes. Diisopropyl azodicarboxylate (0.78 ml) and a solution of thioacetic acid (0.30 g) in anhydrous tetrahydrofuran (1 ml) were dropwise added to the solution while maintaining the temperature of the solution to a level of not higher than 5° C. After stirring the solution for one hour, saturated sodium hydrogen carbonate aqueous solution was added to the reaction solution and the resulting mixture was extracted with ethyl acetate. The resulting organic phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Compound 6-1, 0.43 g).

Workup

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

Sources & evidence

ORD record
ord-6f52e9d208b547f7b74a79847972b500
Source dataset
uspto-grants-2004_01
Patent number
US06683200B2

Reaction notes

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