N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonine → N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonine

HRID 236509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236509
[C:1]([O:18][CH:19]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:20][C:21]([NH:23][C@H:24]([C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH:29]C(OCC1C=CC=CC=1)=O)=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>O1CCCC1.[Pd]>[C:1]([O:18][CH:19]([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:20][C:21]([NH:23][C@H:24]([C:40]([NH:42][C@H:43]([C:47]([OH:49])=[O:48])[C@@H:44]([CH3:46])[OH:45])=[O:41])[CH2:25][CH2:26][CH2:27][CH2:28][NH2:29])=[O:22])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

4

Edukt 1

HCID 86741316N-[Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysyl]-L-threonine

Produkt 1

HCID 53945144N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonineAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-[Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysyl]-L-threonine (2.4 g) prepared by the method of Example 40 was dissolved in tetrahydrofuran (30 ml), and palladium black (0.3 g) added thereto. The mixture was subjected to catalytic hydrogenation at atmospheric pressure. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. Elution with a mixture of chloroform and methanol (50:1) afford powder of N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-lysyl]-L-threonine (1.3 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. washElution
  5. additionwith a mixture of chloroform and methanol (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-9dbe2c0ad1e249e9ba4aaa7c4e69ccff
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04643990

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