Dicyclohexylcarbodiimide → Nalpha-Benzyloxycarbonyl-Nepsilon-(tert.-butyloxycarbo nylglycyl)-L-lysine

HRID 1085078

Reaction equation

HRID 1085078 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([NH:28][CH2:29][C:30](O)=[O:31])=[O:27])([CH3:24])([CH3:23])[CH3:22].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:30](=[O:31])[CH2:29][NH:28][C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 75172N-alpha-Benzyloxycarbonyl-L-lysineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 86744723Nalpha-Benzyloxycarbonyl-Nepsilon-(tert.-butyloxycarbo nylglycyl)-L-lysine

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

9 g of Nα -benzyloxycarbonyl-L-lysine, 5.6 g of tert.-butyloxycarbonylglycine, 3.2 g of triethylamine, 4.9 g of 1-hydroxybenzotriazole and 7.9 g of N,N'-dicyclohexylcarbodiimide are stirred in 100 ml of THF/DMF (7:3) for 1 hour at 0° C. and over night at ambient temperature. After the urea has been filtered off the mixture is concentrated by evaporation, the residue is taken up in ethyl acetate, extracted with saturated KHSO4 solution, washed with water, dried over MgSO4 and concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with methylene chloride/ethyl acetate/methanol (10:1:1). 12.5 g (100% of theory) are obtained in the form of a colourless oil.

Workup

  1. filtrationAfter the urea has been filtered off the mixture
  2. concentrationis concentrated by evaporation
  3. extractionextracted with saturated KHSO4 solution
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe residue is chromatographed over silica gel with methylene chloride/ethyl acetate/methanol (10:1:1)
  8. custom12.5 g (100% of theory) are obtained in the form of a colourless oil

Sources & evidence

ORD record
ord-a65e03c9bb7f4545a9f237ad60342ef3
Source dataset
uspto-grants-1991_04
Patent number
US05008273

Linked notes

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