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

HRID 742047Notes

Reaction equation

HRID 742047 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-778cae4fb092414190142883d4b91611
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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