1-Hydroxybenzotriazole → Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithine

HRID 11847

Reaktionsgleichung

Reaktionsgleichung von HRID 11847
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:42]([N:49]([CH2:57][C:58]1[CH:66]=[CH:65][C:61]([C:62](O)=[O:63])=[CH:60][N:59]=1)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>CN(C=O)C>[C:42]([N:49]([CH2:57][C:58]1[CH:66]=[CH:65][C:61]([C:62]([NH:16][C@H:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[O:63])=[CH:60][N:59]=1)[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][N:52]=1)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009570H-Orn(Z)-OHHCID 219736636-(N-Boc-N-2-picolylaminomethyl)nicotinic Acid

Produkt 1

HCID 86592262Nalpha-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Ndelta-Cbz-L-ornithineAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound obtained in Example 8-6 (165.3 mg) was dissolved in DMF (3 ml). After the addition of WSCI hydrochloride (78.5 mg), HOBt (40.1 mg), and the compound obtained in Example 12-3 (90.4 mg), the mixture was stirred for 23 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform and washed with 1 mol/l aqueous solution of hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (10 g, chloroform/methanol=20/1) to obtain the title compound (167.6 mg) as white foam.

Aufarbeitung

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with 1 mol/l aqueous solution of hydrochloric acid, 1 mol/l aqueous solution of sodium hydroxide, and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue was purified by silica gel column chromatography (10 g, chloroform/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-5d6d23489ab9488382c98bbf6eb9445a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098215B2

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