(Diethylamino)sulfur trifluoride → HCID 66697694, compound

HRID 1819712Notes

Reaction equation

HRID 1819712 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@:5](O)([CH3:23])[C@@H:6]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].CCN(S(F)(F)[F:32])CC.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:25])[C@@:5]([F:32])([CH3:23])[C@@H:6]([C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 67303732HCID 67303732, compound

Product 1

HCID 66697694HCID 66697694, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 43 (36 mg, 0.102 mmol) in anhydrous THF (1.5 mL) is added DAST or Deoxofluor (0.08 mL, 0.68 mmol) at 0° C. under argon. The reaction mixture is stirred at room temperature for 3 h, then cooled down to 0° C., and carefully treated with cold saturated NaHCO3 solution (2 mL). The organic layer is dried over Na2SO4 and concentrated to dryness. The residue is purified by silica gel column chromatography with 1-3% EtOAc in hexanes to give 44 (24.6 mg, 68%) as a syrup. HR-FAB MS; Obsd: m/z 361.1621. Calcd for C18H23O6FLi: m/z 361.1639 (M+H)+.

Workup

  1. temperaturecooled down to 0° C.
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by silica gel column chromatography with 1-3% EtOAc in hexanes

Sources & evidence

ORD record
ord-23ef29a7aa72481780e9c2860c7e1678
Source dataset
uspto-grants-2009_10
Patent number
US07601820B2

Reaction notes

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