Hydrochloric Acid → Methyl(2E)-5-{[4-(trifluoromethyl)benzyl]amino}-5-[4-(trifluoromethyl)phenyl]pent-2-enoate

HRID 1869765Notes

Reaction equation

HRID 1869765 reaction equation
C(S([N:7]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)[CH:8]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[F:34][C:33]([F:35])([F:36])[C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:7][CH:8]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=2)[CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57987395Methyl(2E)-5-{(tert-butylsulfinyl)[4-(trifluoromethyl)benzyl]amino}-5-[4-(trifluoromethyl)phenyl]pent-2-enoate

Product 1

HCID 57987371Methyl(2E)-5-{[4-(trifluoromethyl)benzyl]amino}-5-[4-(trifluoromethyl)phenyl]pent-2-enoateYield 138%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The sulfinamide from Step 3 (450 mg, 0.84 mmol) was dissolved in methanol (3 mL) and the solution was cooled in ice. HCl (4M in dioxane, 0.5 mL) was added and the solution was stirred for 30 min. NaHCO3 was added to neutralize the solution and methanol was removed by evaporation. The residue was extracted into CH2Cl2; this was washed with water, brine, dried (MgSO4) and evaporated and the residue was purified by chromatography on silica using 10-25% ethyl acetate in iso-hexane to give the product (500 mg).

Workup

  1. temperaturethe solution was cooled in ice
  2. customwas removed by evaporation
  3. extractionThe residue was extracted into CH2Cl2
  4. washthis was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customthe residue was purified by chromatography on silica using 10-25% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-019d3a3922824aa799fd8ab04b9315d5
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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