Water → HCID 59389392, compound

HRID 2357957Notes

Reaction equation

HRID 2357957 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]([C:12]1[C:13]2[N:14]([N:20]=[C:21]([C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[CH:22]=2)[C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[CH2:10][CH3:11].O>CS(C)=O>[CH3:19][O:18][C:15]1[N:14]2[N:20]=[C:21]([C:23]([F:29])([F:28])[C:24]([F:25])([F:26])[F:27])[CH:22]=[C:13]2[C:12]([C:9](=[O:8])[CH2:10][CH3:11])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 59389304HCID 59389304, compound

Product 1

HCID 59389392HCID 59389392, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Triethylamine (6.08 mL) was added to a solution of the compound of Example 355 (1.41 g) in dimethylsulfoxide (30 mL). While the solution was stirred at room temperature, sulfur trioxide-pyridine complex (3.46 g) was added and the mixture was stirred at room temperature for 30 min. Water (150 mL) was then added and the resulting crystals were collected by filtration. The crystals were dissolved in ethyl acetate and the solution was dried over anhydrous sodium sulfate. Purification by amino-silica gel column chromatography (ethyl acetate) afforded the title compound as a colorless powder (1.16 g).

Workup

  1. additionsulfur trioxide-pyridine complex (3.46 g) was added
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. filtrationthe resulting crystals were collected by filtration
  4. dissolutionThe crystals were dissolved in ethyl acetate
  5. dry with materialthe solution was dried over anhydrous sodium sulfate
  6. customPurification by amino-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-1a1dcb7a438d4c0cad345e0abc04f2b6
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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