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Sodium cyanoborohydride → (2S)-2-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)amino-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric Acid

HRID 11848
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11848
[C:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][C@H:26]([C:41]([OH:43])=[O:42])[CH2:27][CH2:28][CH2:29][NH:30]C(OCC2C=CC=CC=2)=O)=[O:24])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:44]1[C:53]2[C:52](=O)[CH2:51][CH2:50][CH2:49][C:48]=2[CH:47]=[CH:46][CH:45]=1.C([BH3-])#N.[Na+]>O1CCOCC1.O.CO.C(O)(=O)C.[Pd]>[C:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([NH:25][C@@H:26]([CH2:27][CH2:28][CH2:29][NH:30][CH:52]2[C:53]3[N:44]=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:49][CH2:50][CH2:51]2)[C:41]([OH:43])=[O:42])=[O:24])=[CH:19][N:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]
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Komponenten

8

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-oneHCID 86592262Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithine

Produkt 1

HCID 21043726(2S)-2-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)amino-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric AcidAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidKatalysator
HCID 23938PalladiumKatalysator
HCID 887MethanolLösungsmittel
HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

The compound obtained in Example 12-4 (149.9 mg) was dissolved in a dioxane/water (8/2) solution (7.5 ml). After the addition of 10% Pd—C (154.6 mg), the mixture was stirred for 4.5 hours under hydrogen atmosphere at room temperature. After the reaction, the catalyst was removed by filtration through celite and the solvent was removed by distillation under reduced pressure to obtain a crude product (100.2 mg). 75.4 mg of the crude product was dissolved in methanol (1.5 ml). Then, 5,6,7,8-tetrahydroquinolin-8-one (53.6 mg) and sodium cyanoborohydride (43.2 mg) were added. 25 drops of acetic acid was added to adjust the pH of the mixture to about 5. The mixture was stirred for 22 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1) to obtain the title compound (30.6 mg) as white foam.

Aufarbeitung

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration through celite
  3. customthe solvent was removed by distillation under reduced pressure
  4. customto obtain a crude product (100.2 mg)
  5. stirringThe mixture was stirred for 22 hours at room temperature
  6. customAfter the reaction
  7. customthe solvent was removed by distillation
  8. customThe residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-a446da7f8266422f9bd324e68e376165
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07098215B2

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