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

HRID 1264592Notes

Reaction equation

HRID 1264592 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+].[I-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[C:27]([N+:33]([O-:35])=[O:34])[CH:26]=1>CN(C)C=O>[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])[CH2:29][C:28]1[CH:31]=[CH:32][C:25]([Cl:24])=[CH:26][C:27]=1[N+:33]([O-:35])=[O:34])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 5983994-Chloro-1-(chloromethyl)-2-nitrobenzeneHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Product 1

HCID 18612795Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-nitrobenzyl)amino]propionateYield 115.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.289 g (1 mmol) of methyl 3-hydroxy-2-(4-methoxy-benzenesulfonylamino)propionate in 4 ml of N N-dimethylformamide cooled in an ice bath was added 40 mg of NaH (60% in oil) (1 mmol). After the gas evolution ceased, 0.165 g (1.1 mmol) of sodium iodide was added, followed by the addition of 0.226 g (1.1 mmol) of 4-chloro-2-nitrobenzyl chloride in 1 ml of dimethylformamide. The solution became purple and was stirred at room temperature over the weekend. The solvent was removed under vacuum and the residue extracted with CH2Cl2. The extract was washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 0.53 g of solid which was chromatographed on thick layer silica gel plates with hexane-ethyl acetate (2:1) as solvent to give 0.143 g (31%) of product, as crystals, m.p. 112°-114° C. Anal. for C18H19ClN2O8S: Calc'd: C, 47.2; H, 4.2; N, 6.1; Found: C, 47.0; H, 4.1; N, 6.0.

Workup

  1. customThe solvent was removed under vacuum
  2. extractionthe residue extracted with CH2Cl2
  3. washThe extract was washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-3715a3bfed4d4deebfd9b58dae812b57
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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