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Ethyl Acetate → N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

HRID 85561
Notes
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Reaction equation

HRID 85561 reaction equation
[O:1]=[S:2]1(=[O:23])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])(=[O:13])=[O:12])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][CH2:32][CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C(OCC)(=O)C>CN(C=O)C.O>[Si:35]([O:34][CH2:33][CH2:32][CH2:31][N:10]([CH2:9][CH2:8][N:5]1[CH2:6][CH2:7][S:2](=[O:1])(=[O:23])[CH2:3][CH2:4]1)[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21])(=[O:12])=[O:13])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonate2×HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane2×HCID 68358008N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 68275979N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide
Yield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.400 g, 1.10 mmol) was combined with cesium carbonate (0.538 g, 1.65 mmol) in DMF (5 mL). The slurry was stirred at rt for 30 min, then to it was added (3-bromopropoxy)(tert-butyl)dimethylsilane (0.558 g, 2.20 mmol). The resulting mixture was stirred at rt for 18 h. LCMS indicated incomplete conversion, so additional (3-bromopropoxy)(tert-butyl)dimethylsilane (0.558 g, 2.20 mmol) and cesium carbonate (0.538 g, 1.65 mmol) were added and the mixture was heated to 70° C. for 1 h. Dilution with ethyl acetate (60 mL) and water (40 mL) followed by shaking gave a separation of phases. The organic phase was isolated, washed with water (2×30 mL) and brine (25 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a residue. Purification by silica gel chromatography (gradient 100% DCM to 100:1 DCM:MeOH) gave the title compound as a sticky yellow material, partially crystalline (0.548 g, 93% yield). LCMS: m/z 536 (M+H+), retention time 2.26 min (method 11). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.02 (s, 6H) 0.87 (s, 9H) 1.63-1.75 (m, 2H) 2.72 (t, J=6.40 Hz, 2H) 3.07 (s, 8H) 3.32-3.40 (m, 2H) 3.47 (t, J=6.40 Hz, 2H) 3.56 (t, J=5.90 Hz, 2H) 7.63-7.76 (m, 3H) 8.08 (dd, J=7.53, 1.76 Hz, 1H).

Workup

  1. stirringThe resulting mixture was stirred at rt for 18 h
  2. additionwere added
  3. temperaturethe mixture was heated to 70° C. for 1 h
  4. stirringby shaking
  5. customgave
  6. customa separation of phases
  7. customThe organic phase was isolated
  8. washwashed with water (2×30 mL) and brine (25 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a residue
  12. customPurification by silica gel chromatography (gradient 100% DCM to 100:1 DCM:MeOH)

Sources & evidence

ORD record
ord-4548dc52135c4b719a29999a1c0a1af8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846647B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes