Dicyclohexylcarbodiimide → HCID 131716964, compound

HRID 1534832Notes

Reaction equation

HRID 1534832 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:46][CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][N:52]=[CH:51][CH:50]=1>CN(C)C=O.C(Cl)Cl>[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8].[N:52]1[CH:53]=[CH:54][C:49]([CH2:48][CH2:47][NH-:46])=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 832754-PyridineethanamineHCID 2724635Fmoc-L-Asp(OtBu)-OH

Product 1

HCID 131716964HCID 131716964, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Fmoc-Asp(t-Bu)-OH (Bachem Bioscience) (9.04 g, 22 mmoles) and dicyclohexylcarbodiimide (4.12 g, 20 mmoles) were dissolved in dimethylformamide/methylene chloride (1:5; 50 ml) and cooled in an ice bath. The mixture was stirred for 15 minutes and 4-(2-aminoethyl)-pyridine (2.44 g, 20 mmoles) was added. The combined reaction mixture was stirred overnight and the precipitate was filtered. The filtrate was evaporated to dryness. The residue was redissolved in ethyl acetate (300 ml) and washed with saturated sodium bicarbonate solution (3 times), 0.5N HCl (2 times) and water. The organic layer was dried over sodium sulfate, filtered and the filtrate was evaporated to dryness. The residue was treated with 20% diethylamine/methylene chloride (50 ml) for 1.5 hours, and the reaction mixture was evaporated to dryness and used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe combined reaction mixture
  3. stirringwas stirred overnight
  4. filtrationthe precipitate was filtered
  5. customThe filtrate was evaporated to dryness
  6. dissolutionThe residue was redissolved in ethyl acetate (300 ml)
  7. washwashed with saturated sodium bicarbonate solution (3 times), 0.5N HCl (2 times) and water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. customthe filtrate was evaporated to dryness
  11. additionThe residue was treated with 20% diethylamine/methylene chloride (50 ml) for 1.5 hours
  12. customthe reaction mixture was evaporated to dryness
  13. customused without further purification

Sources & evidence

ORD record
ord-cbeb86b92c414574826a7f3e69ee8271
Source dataset
uspto-grants-1992_02
Patent number
US05091396

Reaction notes

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