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

HRID 1264582Notes

Reaction equation

HRID 1264582 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 15.0 g (51.85 mmol) of methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate in 125 ml of N,N-dimethylformamide, cooled in an ice bath, was added portionwise 2.29 g (57.03 mmol) of NaH (60% in oil). The mixture was stirred at 0° C. for 20 minutes and then a solution of 12.32 g (57.03 mmol) of 2-nitrobenzyl bromide in 25 ml of dry N,N-dimethylformamide was added dropwise. The solution was stirred at room temperature for 48 hours and diluted with 500 ml of ethyl acetate and water. The organic layer was separated and the aqueous layer extracted with 250 ml of ethyl acetate. The combined organic layer and extract was washed with 200 ml each of H2O, 1 N NaHCO3, brine and dried with Na2SO4. The solvent was removed and the residual solid was triturated with ethyl acetate, cooled and filtered to give 13.5 g (61%) of white crystals, having a m.p. 127-129° C. From a small scale run (3.0 g) there was obtained 2.32 g of white crystals, having a m.p. 127-129° C. Anal. for C18H20N2O8S: Calc'd: C, 50.9; H, 4.8; N, 6.6; Found: C, 50.9; H, 4.8; N, 6.5.

Workup

  1. stirringThe solution was stirred at room temperature for 48 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with 250 ml of ethyl acetate
  4. extractionThe combined organic layer and extract
  5. washwas washed with 200 ml each of H2O, 1 N NaHCO3, brine
  6. dry with materialdried with Na2SO4
  7. customThe solvent was removed
  8. customthe residual solid was triturated with ethyl acetate
  9. temperaturecooled
  10. filtrationfiltered

Sources & evidence

ORD record
ord-7abcdfd529bf4d27ab879d426729229b
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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