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

HRID 1720591Notes

Reaction equation

HRID 1720591 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-f1501fff204f4c94b9689f2c3ad2750f
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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