Saccharin → N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharin

HRID 512019

Reaction equation

HRID 512019 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C.O.CCOC(C)=O>[Si:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5](=[O:6])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:1]1(=[O:2])=[O:3])([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:25])[CH3:24]

Participants

7

Reactant 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Product 1

HCID 25018868N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharinYield 45%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of saccharin (92 mg, 0.5 mmol) in anhydrous DMF (4 mL), at room temperature, under a nitrogen atmosphere, was added NaH (60% dispersion in mineral oil, 21 mg, 0.52 mmol). The mixture was stirred at the same temperature for additional 15 min, a solution of (6-bromohexyloxy)-tert-butyldimethylsilane (177 mg, 0.6 mmol) in DMF (1 mL) was added and the resulting mixture microwaved at 150° C. for 10 min. The reaction mixture was cooled to room temperature and diluted with water (5 mL) and AcOEt (10 mL). The organic layer was separated and the aqueous layer extracted with AcOEt (2×10 mL). The combined organic layer was washed with brine, dried (MgSO4) and the solvent removed in vacuum. The residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether) to give 83.8 (89 mg, 45% yield), as a viscous liquid.

Workup

  1. customthe resulting mixture microwaved at 150° C. for 10 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with AcOEt (2×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuum
  7. customThe residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-b27bcf4747144841a9e1fa95fccda40d
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Linked notes

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