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

HRID 1420601Notes

Reaction equation

HRID 1420601 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]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.289 g (1 mmol) of methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)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.

Sources & evidence

ORD record
ord-2e12885b14ce417090493920390c3419
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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