Triethylamine → Z-Lys(BOC)-Phe-OMe

HRID 971546Notes

Reaction equation

HRID 971546 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C:14]([O:16]C1C=CC([N+]([O-])=O)=CC=1)=O)=[O:7])([CH3:4])[CH3:3].[NH2:37][C@H:38]([C:46]([O:48][CH3:49])=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.Cl.C(N(CC)CC)C>CN(C)C=O>[NH:26]([C:27]([O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:28])[C@H:13]([C:14]([NH:37][C@H:38]([C:46]([O:48][CH3:49])=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 135032652212-69-3

Product 1

HCID 131709970Z-Lys(BOC)-Phe-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.0 g of Z-Lys(BOC)-ONP and 10.7 g of H-Phe-OMe.HCl in 70 ml of dimethylformamide are mixed with 6.9 ml of triethylamine at room temperature whilst stirring and the mixture stirred for a further 18 hours. After dilution with ethyl acetate the mixture is washed with potassium carbonate solution until free of nitrophenol, extracted by shaking with 0.1 M citric acid and water, dried over sodium sulphate and evaporated to dryness in vacuo. The protected dipeptide of melting point 78°-80° C. crystalises from ethyl acetate-hexane. Rf = 0.45 in a thin layer chromatogram on silica gel in the system chloroform-acetone (8:2).

Workup

  1. stirringthe mixture stirred for a further 18 hours
  2. washAfter dilution with ethyl acetate the mixture is washed with potassium carbonate solution until free of nitrophenol
  3. extractionextracted
  4. stirringby shaking with 0.1 M citric acid and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness in vacuo
  7. customThe protected dipeptide of melting point 78°-80° C. crystalises from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bd1d9d9c6f9f4b6fa3ce8c9f080d33cf
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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