Sodium hydride → HCID 86755435, compound

HRID 1264574Notes

Reaction equation

HRID 1264574 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH:7]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[N+:25]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]Br)([O-:27])=[O:26]>CN(C)C=O>[OH:9][CH2:8][CH:7]([N:10]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)(=[O:13])=[O:12])[CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[N+:25]([O-:27])=[O:26])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotoluene2×HCID 539780843-Hydroxy-2-(4-methoxybenzenesulfonylamino)-propionic acid tert-butyl ester

Product 1

HCID 86755435HCID 86755435, compoundYield 129.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 6.16 g (18.6 mmol) of 3-hydroxy-2-(4-methoxybenzenesulfonylamino)-propionic acid tert-butyl ester in 50 ml of N,N-dimethylformamide, cooled in an ice bath, was added 0.781 g (19.5 mmol) of sodium hydride. After gas evolution ceased, a solution of 4.02 g (18.6 mmol) of 2-nitrobenzylbromide in 18 ml of N,N-dimethylformamide was added dropwise. The mixture was stirred under nitrogen at room temperature for 4 hours and 1.0 g of 2-nitrobenzyl bromide was added. The mixture was stirred at room temperature overnight and the solvent removed under vacuum. The residue was diluted with water and extracted with CH2Cl2. The organic extract was washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 11.2 g of solid which was chromatographed on silica gel with hexane-ethyl acetate (1:1) as eluent followed by hexane-ethyl acetate (35:65) as eluent. The fractions containing product were combined and the solvent was then removed to gave 7.7 g (89%) of solid. A sample from a 3 mmol run gave a gum. Anal. for C21H26N2O8S: Calc'd: C, 54.1; H, 5.6; N, 6.0; Found: C, 54.0; H, 5.7; N, 6.0.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customthe solvent removed under vacuum
  3. additionThe residue was diluted with water
  4. extractionextracted with CH2Cl2
  5. extractionThe organic extract
  6. washwas washed with H2O, brine
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-40c75c21d8984df291d37751cf8ee7fc
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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