Triethylamine → N-Acetylphenylalanylarginine ethyl ester

HRID 224767

Reaktionsgleichung

Reaktionsgleichung von HRID 224767
[C:1]([NH:4][C@H:5]([C:13]([OH:15])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].Cl.Cl.[CH2:18]([O:20][C:21](=[O:31])[C@H:22]([CH2:24][CH2:25][CH2:26][NH:27][C:28](=[NH:30])[NH2:29])[NH2:23])[CH3:19].C(N(CC)CC)C.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:19][CH2:18][O:20][C:21]([C@@H:22]([NH:23][C:13]([C@@H:5]([NH:4][C:1]([CH3:2])=[O:3])[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:15])[CH2:24][CH2:25][CH2:26][N:27]=[C:28]([NH2:30])[NH2:29])=[O:31]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 74839N-Acetyl-L-phenylalanineHCID 80170N-HydroxysuccinimideHCID 178472568HCID 178472568, Verbindung

Produkt 1

HCID 194320N-Acetylphenylalanylarginine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

0.829 g (4 mmols) of N-acetyl-L-phenylalanine are dissolved in 40 ml of dimethylformamide. 1.10 g (4 mmols) of finely powdered L-arginine ethyl ester dihydrochloride, 0.56 ml (4 mmols) of triethylamine and 0.69 g (6 mmols) of N-hydroxysuccinimide are added and the mixture is cooled to -15° C. After adding 0.91 g (4.4 mmols) of dicyclohexylcarbodiimide, the mixture is stirred at -5° C. for 7 hours, at 5° C. overnight and at room temperature for 5 hours. The precipitate is filtered off and the solution is concentrated almost to dryness in vacuo on a rotary evaporator. After taking up the residue in 80 ml of water, the pH of the solution is adjusted to 6.0 with triethylamine and the solution is discharged onto a column (1.5×40 cm) of Cm- "Sephadex" (Trade Mark) C-25, equilibrated with 0.05 M triethylammonium acetate of pH 6.0. Elution is carried out with a linear gradient increasing to 0.2 M triethylammonium acetate of pH 6.0 (720 ml; 50 ml/hour; size of fraction: 8 ml). Fractions 75-110, which, according to spotting on filter paper and spraying with Sakaguchi reagent, contains most of the eluted material, is lyophilised. 0.5 ml of ethanol is added to the combined residues and the product is precipitated with 60 ml of ethyl acetate. The precipitate is dried over phosphorus pentoxide in a desiccator.

Aufarbeitung

  1. filtrationThe precipitate is filtered off
  2. concentrationthe solution is concentrated almost to dryness in vacuo on a rotary evaporator
  3. washElution
  4. temperatureincreasing to 0.2 M triethylammonium acetate of pH 6.0 (720 ml; 50 ml/hour; size of fraction: 8 ml)
  5. filtrationon filter paper
  6. addition0.5 ml of ethanol is added to the combined residues
  7. customthe product is precipitated with 60 ml of ethyl acetate
  8. dry with materialThe precipitate is dried over phosphorus pentoxide in a desiccator

Quellen und Nachweise

ORD-Eintrag
ord-f80a15044f8b4063a1529cd727d31643
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234477

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