Acetic Acid → N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

HRID 2369963

Reaktionsgleichung

Reaktionsgleichung von HRID 2369963
[C:1]([NH:5][S:6]([CH3:9])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[F:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][CH:17]=1.C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([NH:5][S:6]([CH2:9][C:20]([C:19]1[CH:24]=[CH:25][C:16]([F:15])=[CH:17][CH:18]=1)=[O:21])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 67878Methyl 4-fluorobenzoateHCID 4130162N-tert-butylmethanesulfonamideHCID 178418339Butyllithium

Produkt 1

HCID 68288463N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Under inert gas, 1.00 g of N-tert-butylmethanesulfonamide were initially charged in 20 ml of THF and then, at a temperature of −78° C., 9.00 ml of a 1.6 N butyllithium solution in hexane were added dropwise. After stirring with ice cooling for 5 minutes, the mixture was cooled again to −78° C., and a solution, likewise cooled to −78° C., of 1.33 ml of methyl 4-fluorobenzoate in 10 ml of THF was added dropwise. The mixture was allowed to come to room temperature and stirred for 1 hour. The reaction solution was admixed with 0.82 ml of acetic acid, diluted with 50 ml of ethyl acetate, and washed with 40 ml of saturated aqueous sodium hydrogencarbonate solution and 40 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (662 mg) with a molecular weight of 273.3 g/mol (C12H16FNO3S).

Aufarbeitung

  1. additionwas added dropwise
  2. customto come to room temperature
  3. stirringstirred for 1 hour
  4. washwashed with 40 ml of saturated aqueous sodium hydrogencarbonate solution and 40 ml of saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe crude product was purified by means of normal phase chromatography
  8. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3e55d2e9adfd41718b17b6a18e21a01b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710050B2

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