2,3-Diphenylpropionic acid → 2,3-Diphenylpropionylchloride

HRID 23159

Reaction equation

HRID 23159 reaction equation
[C:1]1([CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:20]>>[C:1]1([CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([Cl:20])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 187442,3-Diphenylpropionic acidHCID 24386Thionyl Chloride

Product 1

HCID 123943832,3-Diphenylpropionylchloride

Procedure

25 g of 2,3-diphenylpropanoic acid was dissolved in 80 mL of SOCl2 (10 eq.). The reaction mixture was stiffed under N2 overnight at room temperature. Extra SOCl2 removed by evaporation. 2,3-Diphenylpropionylchloride (28 g) was obtained as an oil and used without purification. N-(di-BOC-Amidino)-N′-(2,3-diphenylpropionyl)-1,3-diaminoxylene (5′) To a precooled solution (0° C.) of 3 (27.4 g, 72.3 mmol) in 300 mL of CHCl3, Et3N (7.3 g, 72.3 mmol) and 2,3 diphenylpropionylchloride (17.6 g, 72.3 mmol) was added. The mixture was stirred for 1 hour at room temperature. The solution was washed with water and brine and concentrated to dryness. The crude residue was dissolved in minimum amount of EtOAc and 300 mL of hexane was added. 5 (30.1 g, 71% yield) was collected as a white precipitate.

Workup

  1. customExtra SOCl2 removed by evaporation

Sources & evidence

ORD record
ord-708600cdccc0423db30e24dcc72f8c8d
Source dataset
uspto-grants-2005_02
Patent number
US06849733B1

Linked notes

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