Potassium Carbonate → Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoate

HRID 43890

Reaktionsgleichung

Reaktionsgleichung von HRID 43890
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C.[Cu]I>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 143542Ethyl 3-iodobenzoateHCID 145742L-ProlineHCID 15194053-Aminoazetidine, 3-BOC protected

Produkt 1

HCID 68405850Ethyl 3-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}benzoateAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of 3-tert-butoxycarbonylaminoazetidine (300 mg, 1.74 mmol), ethyl 3-iodobenzoate (721 mg, 2.61 mmol) and copper (I) iodide (66 mg, 0.35 mmol), proline (80 mg, 0.70 mmol) and potassium carbonate (721 mg, 5.22 mmol) in DMSO was stirred at 120° C. for two hours. The reaction solution was diluted with ethyl acetate and then filtered. The filtrate was washed with brine and then dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 319 mg of the title compound as a milk white solid (57%).

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-5a04a1605eb34951a9345797ad1dceed
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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