Nicotinic Acid → 3-Methyl-2-[pyridine-3-carbonyl-amino]-pentanoic acid methyl ester

HRID 82480

Reaktionsgleichung

Reaktionsgleichung von HRID 82480
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.[CH3:29][O:30][C:31](=[O:38])[C@H:32]([C@H:34]([CH2:36][CH3:37])[CH3:35])[NH2:33]>C(Cl)Cl>[CH3:29][O:30][C:31](=[O:38])[CH:32]([NH:33][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9])[CH:34]([CH3:35])[CH2:36][CH3:37]

Komponenten

6

Edukt 4

HCID 938Nicotinic AcidHCID 79724-MethylmorpholineHCID 75735L-Isoleucine, methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 673472813-Methyl-2-[pyridine-3-carbonyl-amino]-pentanoic acid methyl esterAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of nicotinic acid (2.0 g, 16.5 mmol) in DCM (20 mL), was added N-methylmorpholine (6.9 mL, 49.5 mmol), EDCI.HCl (6.3 g, 33.0 mmol) and isoleucine methyl ester (3.0 g, 16.5 mmol). The mixture was allowed to stir at room temperature (25° C.) over 2.5 h under nitrogen atmosphere. The resulting mixture was diluted with DCM (200 mL), washed with water (3×100 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was further purified by silica gel column chromatography to obtain product as yellow solid (2.9 g, 72%).

Aufarbeitung

  1. washwashed with water (3×100 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained upon evaporation of the solvent
  4. customwas further purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ee4fc42b7a164947bbb6b4388f3bd1df
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846721B2

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