Dicyclohexylcarbodiimide → HCID 57174957, compound

HRID 1731971Notes

Reaction equation

HRID 1731971 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C@H:4]([CH:16]([CH3:18])[CH3:17])[NH:5]C(OCC1C=CC=CC=1)=O.[CH2:21]([O:28][C:29]([N:31]1[CH2:38][CH2:37][CH2:36][C@H:32]1[C:33]([OH:35])=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>CO.[Pd]>[CH3:1][O:2][CH:3]([O:19][CH3:20])[C@H:4]([CH:16]([CH3:18])[CH3:17])[NH:5][C:33](=[O:35])[C@@H:32]1[CH2:36][CH2:37][CH2:38][N:31]1[C:29]([O:28][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:30]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 101987Benzyloxycarbonyl-L-prolineHCID 56611851HCID 56611851, compound

Product 1

HCID 57174957HCID 57174957, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

24.5 g (0.087 mol) of N-benzyloxycarbonyl-L-valinal dimethyl acetal were dissolved in 200 ml of methanol and the solution was hydrogenated for 2 hours in the presence of 0.5 g of 5% palladium/carbon. After removal of the catalyst by filtration, the solvent was removed by evaporation and the residue was dissolved in 250 ml of dichloromethane. The solution was washed with brine and dried over magnesium sulphate. The solution was then cooled to -20° C. and there were then added 21.8 g (0.087 mol) of N-benzyloxycarbonyl-L-proline followed by 19.8 g (0.096 mol) of N,N'-dicyclohexylcarbodiimide. The solution was stirred at -20° C. for 2 hours and left to stand at 4° C. for 64 hours. The separated N,N'-dicyclohexylurea was removed by filtration and the filtrate was evaporated. The residue was taken up in ethyl acetate, the solution was washed with sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to give an oil. The product was purified by chromatography on 250 g of silica gel using ethyl acetate/hexane (1:1) for the elution. Evaporation of the solution yielded 21.9 g (67%) of N-benzyloxycarbonyl-L-prolyl-L-valinal dimethyl acetal; Rf-value (ethyl acetate): 0.63.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed by evaporation
  4. dissolutionthe residue was dissolved in 250 ml of dichloromethane
  5. washThe solution was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. waitleft
  8. waitto stand at 4° C. for 64 hours
  9. customThe separated N,N'-dicyclohexylurea was removed by filtration
  10. customthe filtrate was evaporated
  11. washthe solution was washed with sodium bicarbonate solution and brine
  12. dry with materialdried over magnesium sulphate
  13. customevaporated
  14. customto give an oil
  15. customThe product was purified by chromatography on 250 g of silica gel
  16. washfor the elution
  17. customEvaporation of the solution

Sources & evidence

ORD record
ord-eaa4a307718d47ef808969acb4a88db0
Source dataset
uspto-grants-1986_11
Patent number
US04623639

Reaction notes

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