Triethylamine → Z-Lys(BOC)-Phe-OMe

HRID 1580872Notes

Reaction equation

HRID 1580872 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].[CH3:37][O:38][C:39]([C@@H:41]([NH2:49])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40].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:49][C@H:41]([C:39]([O:38][CH3:37])=[O:40])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=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 crystallises 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 crystallises from ethyl acetate-hexane

Sources & evidence

ORD record
ord-31c5de2ee3074e8ebdb4bbc98f0fe0df
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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