Dicyclohexylcarbodiimide → HCID 13518680, compound

HRID 1249217Notes

Reaction equation

HRID 1249217 reaction equation
OC(C(F)(F)F)=O.[CH2:8]([O:15][C:16](=[O:31])[C@H:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH2:8]([O:15][C:16](=[O:31])[C@H:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 13518682HCID 13518682, compound

Product 1

HCID 13518680HCID 13518680, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

485 mg of the compound obtained as above was mixed with 10 ml of methylenechloride. 375 mg of β-alanyl-L-phenylalanine benzyl ester TFA salt and 0.11 ml of TEA and 175 mg of DCC were added successively to the mixture under ice-cooling. After 30 minutes, ice-bath was removed and the mixture was stirred overnight. Precipitates formed were removed by filtration, the filtrate was washed with water, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue thus formed was subjected to silicangel column chromatography and eluted with methanol:chloroform (5:95 by v/v ratio) to provide 730 mg of N-[3-decanamidohexanoyloxy)octadecanoyl]-β-alanyl-L-phenylalanine benzyl ester.

Workup

  1. temperaturecooling
  2. customice-bath was removed
  3. customPrecipitates
  4. customformed
  5. customwere removed by filtration
  6. washthe filtrate was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue thus formed
  10. washeluted with methanol:chloroform (5:95 by v/v ratio)

Sources & evidence

ORD record
ord-eb10ba2eea224e2fa61ed480605e5804
Source dataset
uspto-grants-1986_12
Patent number
US04629736

Reaction notes

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