1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide → 5-Oxo-D-prolyl-L-leucyl-L-prolinamide

HRID 851732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851732
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[H][H]>CO.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

Komponenten

5

Edukt 2

HCID 541541661-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 133125035-Oxo-D-prolyl-L-leucyl-L-prolinamideAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

4.48 g (9.5 mmoles) of Z-D-Glp-Leu-Pro-NH2 are dissolved in 200 ml of methanol, 0.9 g of a 10% palladium-on-carbon catalyst are added to the solution, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, and the amorphous residue is triturated with ether. The resulting 3.07 g of crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 2.90 g (90.5%) of D-Glp-Leu-Pro-NH2 are obtained; Rf5 =0.40, [α]D25 =-23.6° (c=1%, in acetic acid).

Aufarbeitung

  1. customis bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe amorphous residue is triturated with ether
  5. dissolutionThe resulting 3.07 g of crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-b36dae216ad14944bbc9132bd1409864
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386073

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