Hydrochloric Acid → methyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

HRID 264296Notes

Reaction equation

HRID 264296 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@@H:4]([CH3:13])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:4]([CH3:13])[C:3]([O:2][CH3:1])=[O:14])(=[O:32])=[O:31])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10987118methyl (2R)-2-(benzylamino)propanoate

Product 1

HCID 54285520methyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-D-alanine methyl ester (~2 g) in methylene chloride (40 mL) containing triethylamine (2.47 mL, 17.7 mmol) is added 4-methoxybenzenesulfonyl chloride (2.44 g, 11.8 mmol). The reaction mixture is stirred overnight at room temperature. The mixture is acidified with 1N HCl and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (10%→20% ethyl acetate/hexanes) to provide methyl 2(R)-[[4-methoxybenzenesulfonyl]-(benzyl)amino]propionate.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by silica gel chromatography (10%→20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4af3bc7dad99444295a3d94bf8de4b32
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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