HCID 67363471, Verbindung → HCID 67364561, Verbindung

HRID 1255492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255492
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd].[Br-].[Zn+2].[Br-]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[NH2:15])[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH3:2]

Komponenten

6

Edukt 2

HCID 67363471HCID 67363471, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67364561HCID 67364561, VerbindungAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 10421208Zinc bromideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of [tert-butoxycarbonyl-(5-chloro-2-nitro-benzyl)-amino]-acetic acid ethyl ester (69.0 g, 0.186 mol) in ethyl acetate (1200 ml) was added zinc bromide (8.5 g, 0.037 mol). The reaction mixture was purged with argon after 15 min. After addition of the palladium catalyst (10% on activated charcoal, 7.9 g, 0.0074 mol) the mixture was hydrogenated at ambient pressure during a period of ca. 48 h until ca. 131 of hydrogen gas had been consumed. The catalyst was removed by filtration and the filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine, each. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (60.6 g, 95.5%) as yellow waxy solid. MS m/e: 343 (M+H+).

Aufarbeitung

  1. customThe reaction mixture was purged with argon after 15 min
  2. customhad been consumed
  3. customThe catalyst was removed by filtration
  4. washthe filtrate was washed with two portions of saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-005cd8c8f00e445187b2d816b792b9bf
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461152B2

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