Sodium Iodide → Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(5-methyl-2-nitrobenzyl)amino]propionate

HRID 1420609Notes

Reaction equation

HRID 1420609 reaction equation
[OH:1][CH2:2][CH:3]([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:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([N+:31]([O-:33])=[O:32])=[C:27]([CH:30]=1)[CH2:28]Cl.[I-].[Na+]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[OH:1][CH2:2][CH:3]([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])[CH2:28][C:27]1[CH:30]=[C:23]([CH3:22])[CH:24]=[CH:25][C:26]=1[N+:31]([O-:33])=[O:32])[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 2724031alpha-Chloro-5-methyl-2-nitrotolueneHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Product 1

HCID 18612748Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(5-methyl-2-nitrobenzyl)amino]propionateYield 0.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 23.14 g (0.08 mol) of methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate in 120 ml of dry N,N-dimethylformamide was added dropwise to a stirred suspension of 3.2 g (0.08 mol) of sodium hydride (57% in oil) in 120 ml of N,N-dimethylformide. When gas evolution ceased, the mixture was chilled in an ice bath and a solution of 16.4 g (0.084 mol) of 5-methyl-2-nitrobenzyl chloride in 100 ml of N N-dimethylformamide was added. To the mixture was added 12.6 g (0.084 mol) of anhydrous sodium iodide and the mixture was chilled in an ice bath and stirred for 20 minutes. The mixture was allowed to warm to room temperature and was stirred overnight. The solvent was removed under vacuum and the residue diluted with 200 ml of H2O and extracted with 500 ml of ethyl acetate. The aqueous layer was extracted with an additional 200 ml of ethyl acetate. The combined extract was washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 41.18 g of crude product. The product was chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent to give 8.14 g (RF 0.38) of product as a yellow semi-solid. From a small scale run (1 mmol) the product was chromatographed twice on thick silica gel plates with hexane-ethyl acetate (1:1) to give 0.12 g of a yellow semi-solid. Anal. for C19H22N2SO8 : Calc'd: C,52.0; H,5.1; N,6.4: Found: C,51.7; H,5.1; N,6.0.

Workup

  1. temperaturethe mixture was chilled in an ice bath
  2. temperaturethe mixture was chilled in an ice bath
  3. stirringwas stirred overnight
  4. customThe solvent was removed under vacuum
  5. additionthe residue diluted with 200 ml of H2O
  6. extractionextracted with 500 ml of ethyl acetate
  7. extractionThe aqueous layer was extracted with an additional 200 ml of ethyl acetate
  8. extractionThe combined extract
  9. washwas washed with H2O, brine
  10. dry with materialdried with Na2SO4
  11. customThe solvent was removed
  12. customto give 41.18 g of crude product
  13. customThe product was chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent
  14. customto give 8.14 g (RF 0.38) of product as a yellow semi-solid

Sources & evidence

ORD record
ord-274f43fe344b4c8092a8d3efe428170b
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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