(Diethylamino)sulfur trifluoride → HCID 11582144, compound

HRID 230807Notes

Reaction equation

HRID 230807 reaction equation
CCN(S(F)(F)[F:7])CC.[CH2:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:37])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH:29](O)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[CH:24][CH:23]=3)=[CH:16][N:15]2[C:38]=1[CH3:39])[CH3:11].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH2:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:37])[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([F:7])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[CH:24][CH:23]=3)=[CH:16][N:15]2[C:38]=1[CH3:39])[CH3:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 57763077HCID 57763077, compound

Product 1

HCID 11582144HCID 11582144, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DAST (20 μL) was added to a chloroform solution (6 mL) of the compound (16 mg) obtained in Example 54, and stirred at room temperature for 5 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform/methanol=90/1) to obtain the entitled compound (10 mg) as a brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline water
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (chloroform/methanol=90/1)

Sources & evidence

ORD record
ord-4278a806a982402eafd1ef0cc407e519
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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