L-Phenylalanine → HCID 272826, compound

HRID 650030Notes

Reaction equation

HRID 650030 reaction equation
[O:1]([CH2:8][C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].[NH2:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1.O>[O:1]([CH2:8][C:9]([NH:18][CH:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]([OH:29])=[O:28])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6140L-PhenylalanineHCID 14798Sodium Hydroxide2×HCID 19188Phenoxyacetic AcidHCID 24386Thionyl Chloride

Product 1

HCID 272826HCID 272826, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6.6 mmol (1.0 g) of phenoxyacetic acid in 15 ml of dioxane is treated with 49.3 mmol (3.6 ml) of thionyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then concentrated. The residue, taken up in 10 ml of dichloromethane, and 7.9 mmol (0.3 g) of sodium hydroxide in 10 ml of water are added in succession to a solution of 7.6 mmol (1.25 g) of phenylalanine and 7.6 mmol (0.3 g) of sodium hydroxide in 10 ml of water, the temperature being maintained at 10° C. The reaction mixture is then stirred for 1 hour at room temperature. After decanting, the aqueous phase is washed with dichloromethane, and then rendered acidic to pH=2 with a dilute hydrochloric acid solution. The precipitate that forms is filtered off and recrystallised from water to yield the expected product.

Workup

  1. concentrationconcentrated
  2. temperaturethe temperature being maintained at 10° C
  3. stirringThe reaction mixture is then stirred for 1 hour at room temperature
  4. customAfter decanting
  5. washthe aqueous phase is washed with dichloromethane
  6. filtrationThe precipitate that forms is filtered off
  7. customrecrystallised from water

Sources & evidence

ORD record
ord-5f3a568f82f544e9983da4ca4a69b9b4
Source dataset
uspto-grants-2001_08
Patent number
US06271247B1

Reaction notes

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