Tetrahydrofuran → HCID 54110952, Verbindung

HRID 1683942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683942
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C@H:7]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH:8]C(OCC1C=CC=CC=1)=O.C1COCC1.[C:40]1([S:50](Cl)(=[O:52])=[O:51])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1>CN(C)C=O.CN(C1C=CN=CC=1)C.[C].[Pd]>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[NH:5][C:6](=[O:23])[C@H:7]([C@H:19]([CH2:21][CH3:22])[CH3:20])[NH:8][S:50]([C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)(=[O:52])=[O:51]

Komponenten

7

Edukt 3

HCID 8028TetrahydrofuranHCID 665601-Naphthalenesulfonyl chlorideHCID 21074402CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

Produkt 1

HCID 54110952HCID 54110952, VerbindungAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 178418390HCID 178418390, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of N-benzyloxycarbonyl-(L)-isoleucyl-(L)-tryptophan methyl ester (11.3 g), palladium-carbon (5%, 50% wet, 3.0 g) and THF (50 ml) was subjected to catalytic hydrogenation at room temperature and atmospheric pressure. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure to yield an oily substance. The oil was dissolved in N,N-dimethylformamide (50 ml), and 1-naphthalenesulfonyl chloride (5.8 g) and 4-(N,N-dimethylamino)pyridine (DMAP) (3.2 g) were added to the ice-cooling mixture. After stirring at 0° C. for 3 hours, the reaction mixture was concentrated under reduced pressure. The residue was suspended in ethyl acetate and the mixture was successively washed with 10% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate and brine, and dried (MgSO4). The organic solvent was evaporated off to yield N-(1-naphthylsulfonyl)-(L)-isoleucyl-(L)-tryptophan methyl ester (9.8 g, 77%) as crystals. Melting point: 172°-174° C.

Aufarbeitung

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto yield an oily substance
  5. temperaturecooling mixture
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. washthe mixture was successively washed with 10% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate and brine
  8. dry with materialdried (MgSO4)
  9. customThe organic solvent was evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-83365a1161e74110bdbc4163de2f18af
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639781

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