1,2-Dichloroethane → 5-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide

HRID 724474

Reaktionsgleichung

Reaktionsgleichung von HRID 724474
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1.Cl.[CH3:15][O:16][NH:17][CH3:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.[Na+].[Cl-]>[CH3:15][O:16][N:17]([CH3:18])[C:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[CH:10][N:9]=1)=[O:13]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 3442Fusaric AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Produkt 1

HCID 587470075-Butyl-pyridine-2-carboxylic acid methoxy-methyl-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5234Sodium ChlorideLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of fusaric acid (896 mg, 5.0 mmol), O,N-dimethylhydroxyl-amine hydrochloride (488 mg, 5 mmol), EDC (1.05 g, 5.5 mmol), HOBT (675 mg, 5.0 mmol) and NEt3 (1.4 ml, 10 mmol) in DMF (100 ml) was stirred at room temperature for 2 h. The reaction mixture was diluted with saturated aqueous NaCl and extracted with EtOAc (2×). The combined organic extracts were washed with 0.5 M citric acid, saturated aqueous NaHCO3, saturated aqueous NaCl, dried, and concentrated under vacuum to, give the desired product I-2A-38a as a viscous oil (940 mg): MS 232.2 (M+1)+; 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 7.60–7.50 (m, 2H), 3.72 (s, 3H), 3.37 (s, 3H), 2.61 (t, 2H, J=7.5Hz), 1.62–1.53 (m, 2H), 1.38–1.28 (m, 2H), 0.89 (t, 3H, J=7.5 Hz).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with 0.5 M citric acid, saturated aqueous NaHCO3, saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated under vacuum to,

Quellen und Nachweise

ORD-Eintrag
ord-40eb3a178e50452b968a27daaac14ed9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141669B2

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