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Citric Acid → Methyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate

HRID 454492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 454492
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CI.[C:32](O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C.O.CN(C)C=O>[C:3]([O:7][C:8]([N:10]([CH3:32])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66989922Methyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate

Produkt 1

HCID 66990621Methyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under ice-cooling, 60% sodium hydride (0.21 g) was added to an N,N-dimethylformamide (15 mL) solution of methyl 4-(2-(tert-butoxycarbonylamino)phenyl)-2-nitrobenzoate (1.3 g), followed by stirring at room temperature for 10 minutes. Then, methyl iodide (0.32 mL) was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. Water, a 10% aqueous solution of citric acid, and diethyl ether were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 1.1 g of methyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate as a light yellow solid.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature for 1 hour
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-ace8e3bc5abb44e7807a4503e9326236
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492582B2

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