Water → HCID 66939511, compound

HRID 1257396Notes

Reaction equation

HRID 1257396 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[S:12][C:13]=1[CH2:14]O.C(N(S(F)(F)[F:32])CC)C.O>C1(C)C=CC=CC=1>[F:32][CH2:14][C:13]1[S:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)=[N:10][C:9]=1[CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 66938994HCID 66938994, compound

Product 1

HCID 66939511HCID 66939511, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (7 mL) of the compound (500 mg, 1.3 mmol) obtained in Example 89c in toluene was added diethylaminosulfur trifluoride (DAST) (650 mg, 4.0 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50) to give the title compound (350 mg, 70%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-025a9ec42b464b7f80ab289502ea754e
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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