4-Fluorobenzoyl chloride → HCID 67547784, compound

HRID 2356759Notes

Reaction equation

HRID 2356759 reaction equation
Cl.[NH2:2][CH:3]([C:8]([C:10]1[S:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:9])[C:4]([O:6][CH3:7])=[O:5].[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[Cl:15][C:12]1[S:11][C:10]([C:8](=[O:9])[CH:3]([NH:2][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][C:17]([F:16])=[CH:18][CH:19]=2)[C:4]([O:6][CH3:7])=[O:5])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 67546821HCID 67546821, compound

Product 1

HCID 67547784HCID 67547784, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-amino-3-(5-chlorothiophen-2-yl)-3-oxopropionate hydrochloride (6.0 g), 4-fluorobenzoyl chloride (4.23 g) and sodium hydrogen carbonate (11.2 g) in ethyl acetate (100 ml) and water (10 ml) was stirred at room temperature for 2 hours. The organic layer was collected, washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with diethyl ether to obtain methyl 3-(5-chlorothiophen-2-yl)-2-(4-fluorobenzoylamino)-3-oxopropionate (7.3 g) as colorless powder.

Workup

  1. customThe organic layer was collected
  2. washwashed 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 diethyl ether

Sources & evidence

ORD record
ord-91dbed50c20d4c35828da3a828d8984a
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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