4-Nitrophenyl chloroformate → 3-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl ester

HRID 2097572

Reaktionsgleichung

Reaktionsgleichung von HRID 2097572
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C([N:27]1[CH2:30][CH:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([I:38])=[CH:34][N:33]=2)[CH2:28]1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:27]2[CH2:28][CH:29]([O:31][C:32]3[CH:37]=[CH:36][C:35]([I:38])=[CH:34][N:33]=3)[CH2:30]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 821294-Nitrophenyl chloroformateHCID 580731012-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine

Produkt 1

HCID 580730963-(5-Iodo-pyridin-2-yloxy)-azetidine-1-carboxylic acid 4-nitro-phenyl esterAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-nitrophenyl chloroformate (692 mg g, 3.44 mmol) was added to a stirred solution of 2-(1-Benzhydryl-azetidin-3-yloxy)-5-iodo-pyridine (1.01 g, 2.29 mol) in dichloromethane (40 mL) at ambient temperature. The resulting solution was stirred at ambient temperature for 18 hr. The solvent was removed in vacuo and the product purified by flash chromatography on silica gel (25 g) eluting with dichloromethane to afford the title compound as a colourless solid (474 mg, 47%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe product purified by flash chromatography on silica gel (25 g)
  3. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c553ef64339c46058acb1272bb741c1d
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450346B2

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