Methanesulfonyl chloride → HCID 136043086, compound

HRID 915962Notes

Reaction equation

HRID 915962 reaction equation
[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][C:18]=4[O:25][CH3:26])=[N:11][C:10]=3[N:9]([CH3:27])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH:1]1([C:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12]([C:17]4[CH:22]=[CH:21][C:20]([N:23]([CH3:24])[S:29]([CH3:28])(=[O:31])=[O:30])=[CH:19][C:18]=4[O:25][CH3:26])=[N:11][C:10]=3[N:9]([CH3:27])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 136043093HCID 136043093, compound

Product 1

HCID 136043086HCID 136043086, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 3 ml pyridine solution of 91.8 mg (0.25 mmol) of the compound obtained in Example 47, 23.2 μl (0.3 mmol) of methanesulfonyl chloride was added, and the mixture was stirred at room temperature for 20 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1˜only ethyl acetate) to obtain 97.2 mg (87%) of the captioned compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1˜only ethyl acetate)

Sources & evidence

ORD record
ord-ef0b42d3eb014a5f89ef2f6b672a536a
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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