(Diethylamino)sulfur trifluoride → HCID 59389401, compound

HRID 2357923Notes

Reaction equation

HRID 2357923 reaction equation
CCN(S(F)(F)[F:7])CC.O[CH:11]([C:13]1[CH:31]=[C:16]2[C:17]([C:23]3[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=3)=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[N:15]2[N:14]=1)[CH3:12]>C(Cl)(Cl)Cl>[F:7][CH:11]([C:13]1[CH:31]=[C:16]2[C:17]([C:23]3[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=3)=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[N:15]2[N:14]=1)[CH3:12]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59389404HCID 59389404, compound

Product 1

HCID 59389401HCID 59389401, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

DAST (51.2 mg) was added dropwise to a solution of the compound of Example 238 (80.0 mg) in chloroform (10 mL) at 0° C. and the mixture was stirred at 0° C. for 30 min. The reaction was quenched by adding a saturated aqueous sodium bicarbonate solution and the reaction 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=1:4) to afford the title compound as a pale yellow powder (30.6 mg).

Workup

  1. customThe reaction was quenched
  2. additionby adding a saturated aqueous sodium bicarbonate solution
  3. extractionthe reaction 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=1:4)

Sources & evidence

ORD record
ord-01d097344a4341919b3951c49ca0263a
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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