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

HRID 1155082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1155082
[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]>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

4

Edukt 1

HCID 541541681-[(Benzyloxy)carbonyl]-5-oxo-L-prolyl-D-leucyl-L-prolinamide

Produkt 1

HCID 133125015-Oxo-L-prolyl-D-leucyl-L-prolinamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3.78 g (8 mmoles) of Z-Glp-D-Leu-Pro-NH2 are dissolved in 150 ml of methanol, 0.8 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, and the residue is triturated with ether. The resulting 2.5 g of amorphous crude product are dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 2.35 g (87%) of Glp-D-Leu-Pro-NH2 are obtained; Rf4 =0.48, [α]D25 =-83.3° (c=1%, in acetic acid).

Aufarbeitung

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether
  5. dissolutionThe resulting 2.5 g of amorphous crude product are dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-367cb3d03ed7428db64c68f6d4166856
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04299821

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