Isoamyl Nitrite → Boc-Leu-DTrp-betaAla-OEt

HRID 129987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129987
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23]N)=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.O1CCOCC1.N(OCCC(C)C)=O.N[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].Cl>CN(C=O)C>[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 8053Isoamyl NitriteHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 11070055Boc-Leu-DTrp-NHNH2HCID 204431481,4-Dioxane hydrochloride

Produkt 1

HCID 131719104Boc-Leu-DTrp-betaAla-OEtAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of Boc-Leu-DTrp-NHNH2 (39 mg) obtained in Example 1-(2) in DMF (0.5 ml) was added 3.1 M HCl/1,4-dioxane (81 μl) at -60° C. The temperature of the solution was raised to -20° C. and isoamyl nitrite (15 μl) was added. The reaction mixture was stirred at -20° C. to -15° C. for 1.5 h and cooled at -60° C. A solution of βAla-OEt.HCl (17 mg) in DMF (0.5 ml) and TEA (50 μl) were added. The reaction mixture was stirred at 5° C. overnight and concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development to give the product (41 mg).

Aufarbeitung

  1. temperaturecooled at -60° C
  2. stirringThe reaction mixture was stirred at 5° C. overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between water and dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development

Quellen und Nachweise

ORD-Eintrag
ord-3462bd9829aa4cf08735b6938a2e38f1
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470833

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