Sodium hydride → Methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionate

HRID 1180554Notes

Reaction equation

HRID 1180554 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+].[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br)([O-:24])=[O:23]>CN(C)C=O.C(OCC)(=O)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])[CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[N+:22]([O-:24])=[O:23])[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Product 1

HCID 18612897Methyl 3-hydroxy-2-[(4-methoxybenzenesulfonyl)-(2-nitrobenzyl)amino]propionateYield 61.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)-propionate (15.0 g 51.85 mmol) in N,N-dimethylformamide (125 ml), cooled in an ice bath, was added, portionwise, NaH (2.29 g 57.03 mmol, 60% in oil). The mixture was stirred at 0° C. for 20 minutes and then a solution of 2-nitrobenzyl bromide (12.32 g 57.03 mmol) in dry N,N-dimethylformamide (25 ml) was added, dropwise. The solution was stirred at room temperature for 48 hours and diluted with ethyl acetate (500 ml) and water. The organic layer was separated and the aqueous layer extracted with additional f ethyl acetate (250 ml). The combined organic layers were washed with water (200 ml), 1N sodium bicarbonate (200 ml), saturated sodium chloride (200 ml) and dried over sodium sulfate The solvent was removed in vacuo and the residual solid was triturated with ethyl acetate, cooled and filtered to give 13.5 g (61%) of white crystals, mp 127-129° C.

Workup

  1. additionwas added
  2. stirringThe solution was stirred at room temperature for 48 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with additional f ethyl acetate (250 ml)
  5. washThe combined organic layers were washed with water (200 ml), 1N sodium bicarbonate (200 ml), saturated sodium chloride (200 ml)
  6. dry with materialdried over sodium sulfate The solvent
  7. customwas removed in vacuo
  8. customthe residual solid was triturated with ethyl acetate
  9. temperaturecooled
  10. filtrationfiltered

Sources & evidence

ORD record
ord-368164dc054049b1b94d126062c551cb
Source dataset
uspto-grants-2007_10
Patent number
US07282496B2

Reaction notes

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