Ethyl iodoacetate → Ethyl (3-benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetate

HRID 1251339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251339
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:19])[NH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O.Cl>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:14]1[C:15]([CH3:18])=[CH:16][CH:17]=[C:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C:13]1=[O:19])[CH3:28]

Komponenten

6

Edukt 3

HCID 12183Ethyl iodoacetateHCID 24758Sodium hydrideHCID 100838403-Benzyloxycarbonylamino-6-methyl-2-pyridone

Produkt 1

HCID 18323889Ethyl (3-benzyloxycarbonylamino-6-methyl-2-oxo-1,2-dihydro-1-pyridyl)acetateAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound of Example 13 (1.80 g, 7.0 mmole) was added to a stirred suspension of sodium hydride (0.33 g, 8.4 mmole) in dry dimethylformamide (50 mL). After 45 minutes, ethyl iodoacetate (1.43 g, 6.7 mmole) was added, and the mixture was stirred overnight, diluted with 10% hydrochloric acid (300 mL) and extracted with ethyl acetate (3×150 mL). The organic layer was washed with brine (twice), dried and evaporated. The resulting yellow, waxy solid was chromatographed, eluting with 3% ethyl acetate in dichloromethane, to give the title compound (1.28 g, 53% yield). Rf=0.52 (silica gel, 5:95 methanol:dichloromethane). Fast atom bombardment mass spectrometry confirmed the theoretical molecular weight of 344.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe organic layer was washed with brine (twice),
  3. customdried
  4. customevaporated
  5. customThe resulting yellow, waxy solid was chromatographed
  6. washeluting with 3% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-d64b7d76651c47e4bc7d5fa0c07378d6
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342504B1

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