Sodium Bicarbonate → HCID 66939419, compound

HRID 1257397Notes

Reaction equation

HRID 1257397 reaction equation
[F:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[N:5][C:4]=1[CH2:18][O:19]C1CCCCO1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CO>[F:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[N:5][C:4]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66939511HCID 66939511, compound

Product 1

HCID 66939419HCID 66939419, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution (10 mL) of the compound (350 mg, 0.93 mmol) obtained in Example 89d in methanol was added p-toluenesulfonic acid monohydrate (530 mg, 2.8 mmol), and the mixture was stirred at 70° C. for 4 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25) to give the title compound (150 mg, 56%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25)

Sources & evidence

ORD record
ord-3c280d27f1fe4da08f46209ec8922ab2
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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