Hydrochloric Acid → HCID 67365197, compound

HRID 1173064Notes

Reaction equation

HRID 1173064 reaction equation
C([N:5]1[CH2:11][C@@H:10]2[C@@H:7]([CH2:8][C@H:9]2[C:12]2[CH:17]=[CH:16][C:15]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH2:6]1)(=O)CC.Cl>C(O)CCC>[CH:7]12[CH2:8][CH:9]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][S:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[CH:24][CH:23]=4)(=[O:20])=[O:21])=[CH:16][CH:17]=3)[CH:10]1[CH2:11][NH:5][CH2:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67366262N-[4-((1R,5S,6R)-3-Propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide

Product 1

HCID 67365197HCID 67365197, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

N-[4-((1R,5S,6R)-3-Propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide (100 mg, 0.21 mmol) was dissolved in n-butanol (10 ml) followed by the addition of concentrated HCl (2 ml). The solution was refluxed for 3 hours, cooled and concentrated. The residue was washed with ethyl acetate, treated with NaOH (2M) and extracted with ethyl acetate (3×10 ml). The alkaline organic extracts were dried over MgSO4, filtered and concentrated to give N-[4-(3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide as an oil (amount 389 mg, yield 98%).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. washThe residue was washed with ethyl acetate
  5. additiontreated with NaOH (2M)
  6. extractionextracted with ethyl acetate (3×10 ml)
  7. dry with materialThe alkaline organic extracts were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f6227dc73e284d929810c4e46764fd15
Source dataset
uspto-grants-2010_11
Patent number
US07834048B2

Reaction notes

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