(Diethylamino)sulfur trifluoride → HCID 59389366, compound

HRID 2357926Notes

Reaction equation

HRID 2357926 reaction equation
CCN(S(F)(F)[F:7])CC.O[C:11]([C:14]1[CH:32]=[C:17]2[C:18]([C:24]3[CH:25]([CH3:31])[CH2:26][C:27](=[O:30])[NH:28][N:29]=3)=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[N:16]2[N:15]=1)([CH3:13])[CH3:12]>C(Cl)(Cl)Cl>[F:7][C:11]([C:14]1[CH:32]=[C:17]2[C:18]([C:24]3[CH:25]([CH3:31])[CH2:26][C:27](=[O:30])[NH:28][N:29]=3)=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[N:16]2[N:15]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59389308HCID 59389308, compound

Product 1

HCID 59389366HCID 59389366, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

DAST (27.9 mg) was added dropwise to a solution of the compound of Example 242 (21.9 mg) in chloroform (5.0 mL) and the mixture was stirred at 0° C. for 30 min. Subsequently, the reaction was quenched by adding a saturated aqueous sodium bicarbonate solution and the mixture was extracted with chloroform (30 mL). The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate. The dried extract was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=1:3→ :4) to afford the title compound as a colorless powder (16.0 mg).

Workup

  1. customSubsequently, the reaction was quenched
  2. additionby adding a saturated aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted with chloroform (30 mL)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. extractionThe dried extract
  7. concentrationwas concentrated
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=1:3→ :4)

Sources & evidence

ORD record
ord-30a14e11a8dd4f869918d223e292f751
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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