Ethyl Acetate → HCID 68410755, compound

HRID 2194722Notes

Reaction equation

HRID 2194722 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]([CH2:22][N:23](C)[C:24](=O)OC(C)(C)C)[S:11][C:12]=1[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[C:32]([O:35]CC)(=[O:34])[CH3:33].Cl.[C:39]([O:42]CC)(=[O:41])[CH3:40]>C(O)C>[C:39]([OH:42])(=[O:41])/[CH:40]=[CH:33]/[C:32]([OH:35])=[O:34].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([CH2:22][NH:23][CH3:24])[S:11][C:12]=1[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 86644405HCID 86644405, compound

Product 1

HCID 68410755HCID 68410755, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl ({4-(2-fluorophenyl)-5-[(3-methoxyphenyl)thio]-2-thienyl}methyl)methylcarbamate (182 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 6 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 to give a free base of the title compound (149 mg). To a solution of fumaric acid (48 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 colorless crystals (yield 118 mg, yield 63%).

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

Sources & evidence

ORD record
ord-814c9293b7404ffb96565387f26c408f
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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