Formic Acid → HCID 23117566, compound
Reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1)([CH2:18][CH:19]=[CH2:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>O1CCCC1>[Cl:28][C:23]1[CH:22]=[C:21]([C:12]([NH:11][CH:1]=[O:2])([CH2:18][CH:19]=[CH2:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:26]=[CH:25][C:24]=1[Cl:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Under cooling on ice, formic acid (140 mL) was added to acetic anhydride (255 mL), followed by stirring at 50° C. for 30 minutes. The reaction mixture was cooled with ice. Subsequently, ethyl 2-amino-2-(3,4-dichlorophenyl)-4-pentenoate (298 g) in tetrahydrofuran (1.5 L) was added to the mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was neutaralized with saturated aqueous sodium bicarbonate. The resultant mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure, to thereby give the title compound (334 g). The title compound was used in the next step without further purification.
Workup
- temperatureThe reaction mixture was cooled with ice
- stirringthe mixture was stirred at room temperature for 30 minutes
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionThe resultant mixture was subjected to extraction with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate anhydrate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-5ff0d1252e8746db844a9e7671c7df61
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07276511B2
Reaction notes
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