Cesium carbonate → 1-Azetidinecarboxylic acid, 3-[(6-nitro-3-pyridinyl)oxy]-, 1,1-dimethylethyl ester

HRID 1918975

Reaktionsgleichung

Reaktionsgleichung von HRID 1918975
I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[N+:13]([C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[N+:13]([C:16]1[N:21]=[CH:20][C:19]([O:22][CH:2]2[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27628576-Nitropyridin-3-olHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Produkt 1

HCID 580436521-Azetidinecarboxylic acid, 3-[(6-nitro-3-pyridinyl)oxy]-, 1,1-dimethylethyl esterAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 199a (2.24 g, 7.9 mmol), 6-nitropyridin-3-ol (1 g, 7.2 mmol) and Cs2CO3 (2.6 g, 7.9 mmol) in DMF (8 mL) was heated at 125° C. in a sealed tube for overnight. The mixture was filtered off and washed with ethyl acetate (20 mL×2). The filtrate was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to give 199b (1.25 g, 59%). MS: [M+H]+ 296.

Aufarbeitung

  1. filtrationThe mixture was filtered off
  2. washwashed with ethyl acetate (20 mL×2)
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified on reverse phase Combi-flash

Quellen und Nachweise

ORD-Eintrag
ord-3b479691a5c04ba6bb467ac3ca4fd31b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618107B2

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