4-Fluorobenzoyl chloride → HCID 67546994, compound

HRID 2356740Notes

Reaction equation

HRID 2356740 reaction equation
Cl.[NH2:2][CH:3]([C:10]([C:12]1[S:13][C:14]([Cl:17])=[CH:15][CH:16]=1)=[O:11])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Cl:17][C:14]1[S:13][C:12]([C:10](=[O:11])[CH:3]([NH:2][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=2)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 67546526HCID 67546526, compound

Product 1

HCID 67546994HCID 67546994, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of ethyl 3-amino-4-(5-chlorothiophen-2-yl)-4-oxobutyrate hydrochloride (596 mg), 4-fluorobenzoyl chloride (380 mg) and sodium hydrogen carbonate (1.0 g) in ethyl acetate (10 ml) and water (10 ml) was stirred at room temperature for 2 hours. To the reaction mixture were added ethyl acetate (30 ml) and water (30 ml), and the organic layer was collected. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with hexane to obtain a crude product of ethyl 4-(5-chlorothiophen-2-yl)-3-[(4-fluorobenzoyl)amino]-4-oxobutyrate (732 mg) as colorless powder.

Workup

  1. customthe organic layer was collected
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-982792f3698d47e79b079821895a9e84
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

Loading…