Acetonitrile → HCID 59086190, compound

HRID 1176150Notes

Reaction equation

HRID 1176150 reaction equation
C(#N)C.[CH2:4]([CH:6]([CH2:23][CH3:24])[C@H:7]([NH:10][S:11]([C:14]1[S:15][C:16]([Sn](C)(C)C)=[CH:17][CH:18]=1)(=[O:13])=[O:12])[CH2:8][OH:9])[CH3:5].[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(OCC)(=O)C>[CH2:23]([CH:6]([CH2:4][CH3:5])[C@H:7]([NH:10][S:11]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(=[O:12])=[O:13])[CH2:8][OH:9])[CH3:24]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724933SelectfluorHCID 66929698HCID 66929698, compound

Product 1

HCID 59086190HCID 59086190, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred mixture of anhydrous acetonitrile (6 mL) and N-[(1S)-2-ethyl-1-(hydroxymethyl)butyl]-5-(trimethylstannyl)thiophene-2-sulfonamide (0.24 g, 0.56 mmol) was added Selectfluor (Aldrich) (0.204 g, 0.57 mmol) all at once. The mixture was heated to 75° C. under a nitrogen atmosphere, stirred 16 h and then cooled to 25° C. and filtered. Evaporation of the solvent produced a crude solid that was taken up in ethyl acetate and again filtered to remove insoluble solids. Evaporation of the remaining solvent produced an oil that was purified by flash chromatography using hexane-ethyl acetate 2-1 as eluant, producing the title compound as the major product (0.051 g, 33%). MS (−ESI) 276.20 ([M−H]−).

Workup

  1. temperaturecooled to 25° C.
  2. filtrationfiltered
  3. customEvaporation of the solvent
  4. customproduced a crude solid
  5. filtrationagain filtered
  6. customto remove insoluble solids
  7. customEvaporation of the remaining solvent
  8. customproduced an oil that
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-bdd6816edf8a4893a6dc55e3c7be3dc4
Source dataset
uspto-grants-2010_11
Patent number
US07842718B2

Reaction notes

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