Dichloromethane → L-Phenylalanine, methyl ester

HRID 642940Notes

Reaction equation

HRID 642940 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

L-Phenylalanine methyl ester hydrochloride (4.9 g) was dissolved in water (25 mL) in a 100 mL round bottom flask and stirred at room temperature. Sodium carbonate (3.1 g) in water (12.5 mL) was added in 3 minutes. The reaction mixture was stirred for 5 minutes at room temperature. Dichloromethane (25 mL) was added and the reaction mixture was stirred 5 minutes. The aqueous solution was transferred to a 125 mL separating funnel. The organic layer was collected. The aqueous layer was extracted twice with 12.5 mL of dichloromethane. The three organic extractions were combined, dried with magnesium sulfate (6 g), filtered to remove the magnesium sulfate and concentrated to give L-phenylalanine methyl ester free base.

Workup

  1. stirringThe reaction mixture was stirred for 5 minutes at room temperature
  2. stirringthe reaction mixture was stirred 5 minutes
  3. customseparating funnel
  4. customThe organic layer was collected
  5. extractionThe aqueous layer was extracted twice with 12.5 mL of dichloromethane
  6. extractionThe three organic extractions
  7. dry with materialdried with magnesium sulfate (6 g)
  8. filtrationfiltered
  9. customto remove the magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3a7e7dd0bfda4909b033821a7dacb78b
Source dataset
uspto-grants-2010_04
Patent number
US07696372B2

Reaction notes

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