Sodium Carbonate → HCID 89668435, Verbindung

HRID 1482210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482210
[C:1](Cl)(=[O:17])[O:2][CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[N+:14]([O-:16])=[O:15].[CH2:19]([S:21][S:22][CH2:23][C@H:24]([NH:28][CH3:29])[C:25]([OH:27])=[O:26])[CH3:20].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>O1CCOCC1.O>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:4]([CH2:3][O:2][C:1]([N:28]([CH3:29])[C@@H:24]([CH2:23][S:22][S:21][CH2:19][CH3:20])[C:25]([OH:27])=[O:26])=[O:17])=[C:5]([N+:14]([O-:16])=[O:15])[CH:6]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 3084878((Nitroveratryl)oxy)chlorocarbamateHCID 89668341HCID 89668341, Verbindung2×

Produkt 1

HCID 89668435HCID 89668435, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4,5-Dimethoxy-2-nitrobenzyl carbonochloridate (394 mg, 1.43 mmol) was added to a solution of (R)-3-(ethyldisulfanyl)-2-(methylamino)propanoic acid (Compound 2f-F) (232 mg, 1.19 mmol) and sodium carbonate (252 mg, 2.38 mmol) in dioxane (3 ml) and water (3 ml), and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution (3 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100) to afford (R)-2-((((4,5-dimethoxy-2-nitrobenzyl)oxy)carbonyl)(methyl)amino)-3-(ethyldisulfanyl)propanoic acid (Compound 2k-F) (483 mg, 93%).

Aufarbeitung

  1. extractionafter which the mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. extractionThe organic extract
  4. dry with materialwas then dried over magnesium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=70/30→0/100)

Quellen und Nachweise

ORD-Eintrag
ord-e891292b2bab4a0bb7d0738c4f2ed099
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409952B2

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