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

HRID 1720588Notes

Reaction equation

HRID 1720588 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-08a8b6f35b9744a0bd3f0190fe54157b
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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