Ethyl bromoacetate → Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetate

HRID 264312

Reaktionsgleichung

Reaktionsgleichung von HRID 264312
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 741351N-benzyl-4-methoxybenzenesulfonamide

Produkt 1

HCID 3503631Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (1.56 g of a 50% oil dispersion, 33.0 mmol) is suspended in tetrahydrofuran (85 mL). To this is added a solution of N-[4-methoxybenzenesulfonyl]-benzylamine (9.0 g, 32.5 mmol) also in tetrahydrofuran (85 mL), and the reaction is stirred for 30 minutes at room temperature. Then ethyl bromoacetate (5.40 mL, 48.8 mmol) is added, and the reaction is stirred overnight at room temperature. The reaction is quenched with a small amount of water, and all the solvent is removed. The crude mixture is partitioned between ethyl acetate and water, the aqueous phase is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (30% ethyl acetate/hexane) to give ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetate.

Aufarbeitung

  1. stirringthe reaction is stirred overnight at room temperature
  2. customThe reaction is quenched with a small amount of water, and all the solvent
  3. customis removed
  4. customThe crude mixture is partitioned between ethyl acetate and water
  5. extractionthe aqueous phase is extracted several times with ethyl acetate
  6. dry with materialthe combined organic layers are dried (Na2SO4)
  7. customthe solvent is evaporated
  8. customThe product is purified by silica gel chromatography (30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-69b12a99fb6745e3a0dca42796a9ff98
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646167

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