4-Phenylbenzoyl chloride → HCID 11046468, compound

HRID 1519682Notes

Reaction equation

HRID 1519682 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=[CH:14][C:10]([C:11]([NH:17][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

Product 1

HCID 11046468HCID 11046468, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Phenylbenzoyl chloride (4.3 g) was added little by little to a chloroform (80 mL) solution of diethyl aminopropanedioate hydrochloride (4.3 g) and TEA (8.4 mL) under ice cooling, and the mixture was stirred for 3 hours at the same temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and the desiccant was filtered out. Then, the solvent was distilled off under reduced pressure, and the resulting residue was purified by OH type silica gel column chromatography (chloroform/methanol=20/1) to obtain diethyl [(biphenyl-4-ylcarbonyl)amino]propanedioate (white solid) (6.7 g, 95%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by OH type silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-76cae45ea50b49f491871e5f0216fc9e
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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