Potassium Hydroxide → HCID 53805939, Verbindung

HRID 1789882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789882
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:18]([Cl:20])[CH:19]=1)[C:8]([O:10]CC)=[O:9])[CH3:4]>C(O)C.C(Cl)Cl>[CH2:3]([O:5][C:6](=[O:29])[CH:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:18]([Cl:20])[CH:19]=1)[C:8]([OH:10])=[O:9])[CH3:4]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 53978298HCID 53978298, Verbindung

Produkt 1

HCID 53805939HCID 53805939, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of KOH (0.44 g, 6.72 mmol, 85%) in ethanol (5 ml) was added to a solution of 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid diethyl ester (2.45 g, 6.11 mmol) in ethanol (25 ml) and methylene chloride (10 ml) at 0° C. The mixture was stirred for 18 h at room temperature. The solvent was evaporated in vacuo and the residue dissolved in water. The aqueous layer was washed with ether, acidified to pH 4 by 1 M HCl and extracted with methylene chloride and ethyl acetate. The combined organic layers were washed with water and brine and dried. Filtration and concentration under reduced pressure gave the crude product which was purified by flash chromatography (10% MeOH in CH2Cl2) giving 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.41 g, 62%) as a yellow-white glassy foam.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in water
  3. washThe aqueous layer was washed with ether
  4. extractionextracted with methylene chloride and ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. customdried
  7. filtrationFiltration and concentration under reduced pressure
  8. customgave the crude product which
  9. customwas purified by flash chromatography (10% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-f503dbc19a7340f9b5be2c028eee0c01
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071175B1

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