Hydrochloric Acid → beta-phenylpropionyl-L-phenylalanine

HRID 1368887Notes

Reaction equation

HRID 1368887 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[C:15](Cl)(=[O:24])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>O1CCOCC1.O>[C:4]1([CH2:3][C@H:2]([NH:1][C:15](=[O:24])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([OH:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 14798Sodium Hydroxide2×HCID 64801Benzenepropanoyl chloride

Product 1

HCID 47590beta-phenylpropionyl-L-phenylalanineYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

L-phenylalanine (2 g) was dissolved in a mixed solvent of dioxane:water=1:1 (20 ml), and the reaction system was cooled to 0° C. The solution was added with 1 N aqueous sodium hydroxide (12.1 ml), and further added dropwise with 1 N aqueous sodium hydroxide (12.1 ml) and hydrocinnamoyl chloride (1.98 ml) simultaneously over 25 minutes, and then stirred at 0° C. for 2 hours. 1 N Hydrochloric acid was added to the mixture to adjust the pH to 3, and the precipitated crystals were washed with water and diethyl ether to obtain 3-phenyl-(2S)-(3-phenylpropanoylamino)propanoic acid (2.9 g, 79.9%).

Workup

  1. washthe precipitated crystals were washed with water and diethyl ether

Sources & evidence

ORD record
ord-c4550a42db7d405ab00f72533e4cacd2
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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