Methyl p-toluenesulfonate → HCID 11546988, compound

HRID 445141Notes

Reaction equation

HRID 445141 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:24][C:23]3([CH2:26][CH2:25]3)[C:15]3[C:16]4[C:17](=[N:22][C:14]=3[CH:13]2[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[NH:18][CH:19]=[CH:20][CH:21]=4)=[O:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:34]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[C:4]([NH:9][C:10]([N:12]2[CH2:24][C:23]3([CH2:26][CH2:25]3)[C:15]3[C:16]4[C:17](=[N:22][C:14]=3[CH:13]2[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[N:18]([CH3:34])[CH:19]=[CH:20][CH:21]=4)=[O:11])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 10340Sodium CarbonateHCID 178425243HCID 178425243, compound

Product 1

HCID 11546988HCID 11546988, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound (188 mg) prepared in Example 15 was suspended in toluene (8 mL) and methyl p-toluenesulfonate (0.32 mL) was added, followed by refluxing for 2 hours. After the reaction solution was air-cooled, an aqueous saturated sodium carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→methylene chloride:methanol=85:15) to obtain the titled compound having the following physical properties (122 mg).

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction solution was air-cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→methylene chloride:methanol=85:15)

Sources & evidence

ORD record
ord-c15e0e37d49142d4baa9c74cbeffde5e
Source dataset
uspto-grants-2013_07
Patent number
US08476293B2

Reaction notes

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