Potassium Carbonate → Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate

HRID 1784298

Reaktionsgleichung

Reaktionsgleichung von HRID 1784298
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[C:15]([NH:22][CH2:23][CH2:24][CH2:25][NH2:26])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:18]([O:17][C:15]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Produkt 1

HCID 67235341Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-fluoro-4-nitrobenzoate (5.8 g, 1 eq), N-Boc-1,3-diaminopropane (5.75 g, 1.1 eq) and potassium carbonate (8.04 g, 2 eq) in acetonitrile (200 ml) is heated under reflux for 2 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (100 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. The solid obtained is washed with petroleum ether and dried (10.2 g; 99% yield).

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. concentrationthen concentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customThe solid obtained
  9. washis washed with petroleum ether
  10. customdried (10.2 g; 99% yield)

Quellen und Nachweise

ORD-Eintrag
ord-def1084f0c3b4f64b72985ba2b88a4e8
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501525B2

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