Benzyl Bromide → Methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

HRID 2209679Notes

Reaction equation

HRID 2209679 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:20])[C@H:6]([CH3:19])[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([N:7]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]([CH3:19])[C:5]([O:4][CH3:3])=[O:20])(=[O:9])=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 7081982N-[4-methoxybenzenesulfonyl]-alanine methyl ester

Product 1

HCID 22907154Methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.60 g, 11.0 mmol) in dimethylformamide (20.0 mL), is added N-[4-methoxybenzenesulfonyl]-alanine methyl ester (2.6 g, 10.0 mmol) in dimethylformamide (10.0 mL). After stirring at room temperature for 30 minutes, benzyl bromide (1.22 mL, 10.0 mmol) is added, and the reaction is stirred for two hours at room temperature. The reaction is then partitioned between ether and brine, the organic layer is dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (20% ether/hexanes)to give methyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]-propionoate.

Workup

  1. stirringthe reaction is stirred for two hours at room temperature
  2. customThe reaction is then partitioned between ether and brine
  3. dry with materialthe organic layer is dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (20% ether/hexanes)

Sources & evidence

ORD record
ord-850f509113e14e31a7618c632424a5df
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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