(Diethylamino)sulfur trifluoride → HCID 11295543, compound

HRID 412858Notes

Reaction equation

HRID 412858 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:13][CH2:14][C@H:15]1[O:21][CH:19](O)[C@H:18]([N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C@@H:17]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@H:16]1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:12])[CH3:11]>ClCCCl.C(OCC)(=O)C>[C:10]([O:13][CH2:14][C@H:15]1[O:21][C@@H:19]([F:7])[C@H:18]([N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C@@H:17]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@H:16]1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 53840937HCID 53840937, compound

Product 1

HCID 11295543HCID 11295543, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen gas atmosphere, diethylaminosulfur trifluoride (5.8 ml, 43.9 mmol) was added to a solution of Compound 23 (5.95 g, 11.2 mmol) in 1,2-dichloroethane (50 ml) under ice cooling, and the mixture was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, and dried over magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=4:1) to obtain Compound 24 (5.9 g, 99%).

Workup

  1. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThen, the solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-64e027307b734b36b027d09c04cc943a
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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