Dicyclohexylcarbodiimide → HCID 86734647, compound

HRID 328591Notes

Reaction equation

HRID 328591 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C@H:5]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH3:2].O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:22])[C@H:5]([CH2:17][CH2:18][C:19]([O:21][N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=[O:30])=[O:20])[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 10470569HCID 10470569, compound

Product 1

HCID 86734647HCID 86734647, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-CBZ-L-glutamic acid-α-ethyl ester (0.096 mole, 29.6 g.) and N-hydroxysuccinimide (0.1 mole, 11.5 g.) in 200 ml. of dioxane was added with stirring at room temperature (0.1 mole, 21 g.) of dicyclohexylcarbodimide. After stirring 24 hours at room temperature, the mixture was filtered to remove dicyclohexylurea. The filtrate was concentrated in vacuo to give an oil. This oil failed to crystallize and was used in the next step without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove dicyclohexylurea
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an oil
  5. customto crystallize
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2f6d879876b742f58beb13accfaebd9e
Source dataset
uspto-grants-1977_04
Patent number
US04017636

Reaction notes

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