Potassium Carbonate → Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate

HRID 525997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525997
[O:1]=[C:2]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][N:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+]>CO>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:2](=[O:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N:11][CH:12]=1)#[CH:17]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 89444199Methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate

Produkt 1

HCID 89443928Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate (26 mg, 0.085 mmol) in methanol, potassium carbonate (5.90 mg, 0.042 mmol) is added in one portion and the reaction mixture is stirred at room temperature for 2 h. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was dried on magnesium sulfate and concentrated under vacuum to give methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate A41 (12 mg, 60% yield). 1H NMR (400 MHz, CDCl3) 8.39 (d, 1H), 8.16 (m, 2H), 7.77 (d, 1H), 3.72 (s, 3H), 2.74 (m, 4H) ppm.

Aufarbeitung

  1. customthe solution was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. customThe combined organic layer was dried on magnesium sulfate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-511d2a41211c4fe792dc6bbe6036081d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345244B2

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