Hydrochloric Acid → HCID 23114655, compound

HRID 2080482Notes

Reaction equation

HRID 2080482 reaction equation
C(O)C.C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([CH:17]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:14]([CH3:36])=[CH:13][N:12]=1)(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([S:26]([CH:17]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[C:15]2[C:14]([CH3:36])=[CH:13][N:12]=[C:11]([NH2:10])[CH:16]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 58734256HCID 58734256, compound

Product 1

HCID 23114655HCID 23114655, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ethanol (5 ml) solution of t-butyl[4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-methylpyridin-2-yl]carbamate (200 mg, 0.393 mmol) was added concentrated hydrochloric acid (6 ml). The resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue thus obtained was added a saturated aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was recrystallized from hexane:ethyl acetate to give the title compound (125 mg, 0.306 mmol, 78%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo the residue thus obtained
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed sequentially with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-eef4682134664a69aff9ce4632dee55e
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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