Ethyl Acetate → HCID 54394959, Verbindung

HRID 1789811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789811
[CH3:1][CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[C:17]([O:21][C:22](=[O:32])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][N:25]=1)([CH3:20])([CH3:19])[CH3:18].CCOC(C)=O>CN(C=O)C.CCCCCCC.CCOC(C)=O>[CH2:13]([O:12][C:10](=[O:11])[C:2]([CH2:30][C:27]1[CH:26]=[N:25][C:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:32])=[CH:29][CH:28]=1)([CH3:1])[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])[CH3:14]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 13198666tert-Butyl ethyl methylpropanedioateHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Produkt 1

HCID 54394959HCID 54394959, VerbindungAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 21899848Ethylacetate heptaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl ethyl methylmalonate (457 mg, 2.26 mmol) in DMF (4 mL) was added dropwise to a suspension of NaH (90 mg, 2.26 mmol, 60% in oil) in DMF (4 mL). The reaction mixture was stirred for 20 min. A solution of (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.74 mmol) in DMF (2.5 mL) was added and the reaction was stirred for 70 min. EtOAc was added and the mixture was washed with water and brine, dried and concentrated under reduced pressure. Chromathography (Heptane/EtOAc, 3:1→1:3) gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid tert-butyl ester ethyl ester (437 mg, 61% yield).

Aufarbeitung

  1. stirringthe reaction was stirred for 70 min
  2. washthe mixture was washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8a92e98d3404dbf8bf128e5eee8b1de
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071175B1

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