Ethyl Acetate → HCID 68411867, compound

HRID 2194723Notes

Reaction equation

HRID 2194723 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH2:23][N:24](C)[C:25](=O)OC(C)(C)C)[S:11][C:12]=1[S:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[O:14].[C:33]([O:36]CC)(=[O:35])[CH3:34].Cl.[C:40]([O:43]CC)(=[O:42])[CH3:41]>C(O)C>[C:40]([OH:43])(=[O:42])/[CH:41]=[CH:34]/[C:33]([OH:36])=[O:35].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH2:23][NH:24][CH3:25])[S:11][C:12]=1[S:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[O:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86644406HCID 86644406, compound

Product 1

HCID 68411867HCID 68411867, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl ({4-(2-fluorophenyl)-5-[(3-methoxyphenyl)sulfinyl]-2-thienyl}methyl)methylcarbamate (231 mg) was dissolved in ethyl acetate (3 mL) and ethanol (1 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added at room temperature. After stirring for 4 hr, the reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9) to give a free base of the title compound (155 mg) as a pale-yellow oil. To a solution of fumaric acid (50 mg) in ethanol (10 mL) was added a solution of the obtained free base in ethyl acetate (5 mL), and the solvent was evaporated under reduced pressure. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and 2-propanol to give the title compound as a white powder (yield 118 mg, yield 50%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9)

Sources & evidence

ORD record
ord-54fa46bab1c84f7abc4f5c4b8be1889c
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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