1-Hydroxybenzotriazole → 3-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-{2-[(S)-1-(carbamoyl)ethylcarbamoyl]-2-methylpropoxy}phenyl)-methyl]-5-isopropyl-1H-pyrazole

HRID 1442386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1442386
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([C:42](O)=[O:43])([CH3:41])[CH3:40])=[CH:33][CH:32]=2)=[C:28]([CH:45]([CH3:47])[CH3:46])[NH:27][N:26]=1)(=[O:3])[CH3:2].Cl.[NH2:49][C@H:50]([C:52]([NH2:54])=[O:53])[CH3:51].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([C:42](=[O:43])[NH:49][C@H:50]([C:52](=[O:53])[NH2:54])[CH3:51])([CH3:41])[CH3:40])=[CH:33][CH:32]=2)=[C:28]([CH:45]([CH3:47])[CH3:46])[NH:27][N:26]=1)(=[O:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 68540296HCID 68540296, Verbindung

Produkt 1

HCID 685388053-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-{2-[(S)-1-(carbamoyl)ethylcarbamoyl]-2-methylpropoxy}phenyl)-methyl]-5-isopropyl-1H-pyrazoleAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-4-{[4-(2-carboxy-2-methylpropoxy)phenyl]-methyl}-5-isopropyl-1H-pyrazole (0.13 g) in N,N-dimethyl-formamide (2 mL) were added L-alanine amide hydrochloride (46 mg), triethylamine (0.08 mL), 1-hydroxybenzotriazole (38 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=20/1-10/1) to give the title compound (0.14 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=20/1-10/1)

Quellen und Nachweise

ORD-Eintrag
ord-6e4e460687074e87a832124e7fc551f0
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655632B2

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