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

HRID 1393845Notes

Reaction equation

HRID 1393845 reaction equation
[CH2:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>O1CCCC1>[CH2:1]([N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 741351N-benzyl-4-methoxybenzenesulfonamide

Product 1

HCID 3503631Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetateYield 143.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-benzyl-4-methoxybenzenesulfonamide (15.00 g, 36.06 mmol) in tetrahydrofuran (90 ml) was added to a suspension of sodium hydride (60% oil suspension 1.47 g, 36.78 mmol) in tetrahydrofuran (90 ml) and stirred for 50 minutes at room temperature. Then the suspension, with ethyl bromoacetate (6.00 ml, 54.09 mmol) added thereto, was stirred for 14 hours at room temperature. After the reaction, the mixture, with water (100 ml) added thereto, was extracted with ethyl acetate (100 ml×3). The organic layer was dried over sodium sulfate, and then the solvent was evaporated out. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane), to give ethyl 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}acetate (18.82 g, 96%).

Workup

  1. stirringwas stirred for 14 hours at room temperature
  2. customAfter the reaction
  3. extractionwas extracted with ethyl acetate (100 ml×3)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated out
  6. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23aa93e68d544ca4b2ae9ca7af7d316d
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

Loading…