1-Hydroxybenzotriazole → (1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamide

HRID 1791131

Reaktionsgleichung

Reaktionsgleichung von HRID 1791131
[C:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:24]([OH:26])=O)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].[NH2:27][C@@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29]([NH2:31])=[O:30].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O.C(N(CC)CC)C>[NH3:4].[C:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]2[C:24]([NH:27][C@@H:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]([NH2:31])=[O:30])=[O:26])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 729986(S)-(+)-2-Phenylglycine amideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59111308(1R,2R)-2-(4-{[Acetyl(2-pyridinyl)amino]methyl}phenyl)cyclohexanecarboxylic acid

Produkt 2

HCID 222AmmoniaHCID 10227912(1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamideAusbeute 128,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

(1R,2R)-2-(4-{[Acetyl(2-pyridinyl)amino]methyl}phenyl)cyclohexanecarboxylic acid (0.44 g) is suspended in DMF (15 ml), (2S)-2-amino-2-phenylethanamide (0.37 g), triethylamine (0.68 ml), 1-hydroxybenzotriazole (0.18 g) and EDC hydrochloride (0.27 g) are admixed and the mixture is stirred at room temperature for 2 days. The suspension is diluted with water and extracted with dichloromethane and the organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. Chromatography (silica gel, dichloromethane:methanol:saturated aqueous ammonia solution=50:1:0.05 to 20:1:0.05 gives (1R,2R)-2-(4-{[acetyl(2-pyridinyl)amino]methyl}phenyl)-N-[(1S)-2-amino-2-oxo-1-phenylethyl]cyclohexanecarboxamide (0.39 g) as a colourless solid.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washthe organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5c4064311ea74a27a6cc0b7160ecaad2
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074780B2

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