Potassium Carbonate → L-Phenylalanine, methyl ester

HRID 980521Notes

Reaction equation

HRID 980521 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.[K+].[K+].C(N[C@@H]1C(=O)OC(=O)C1)=O>C(OCC)(=O)C.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

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of L-phenylalanine methyl ester in ethyl acetate is prepared by dissolving 11 g (0.05 moles) of L-phenylalanine methyl ester hydrochloride in 50 ml of water and then adding 6 g of K2CO3. The aqueous solution thus obtained is extracted twice, each time with 100 ml of ethyl acetate. The organic layers obtained in this manner are added together, dried over anhydrous Na2SO4, and concentrated under reduced pressure to a final volume of 50 ml. 30 ml of ethyl adetate, 7.2 g (0.05 moles) of N-formyl-L-aspartic anhydride and 1.0 g of the commercial cation exchange resin DOWEX 50 W (of the Dow Chemical Company), previously dried at 50° C. under vacuum to constant weight, are fed into a reaction flask of 500 ml capacity, fitted with an agitator and dropping funnel.

Workup

  1. customThe aqueous solution thus obtained
  2. extractionis extracted twice
  3. customThe organic layers obtained in this manner
  4. additionare added together
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure to a final volume of 50 ml
  7. customare fed into a reaction flask of 500 ml capacity
  8. customfitted with an agitator

Sources & evidence

ORD record
ord-fa356e3dd7c4412fb32b58bd0553a2c0
Source dataset
uspto-grants-1987_01
Patent number
US04638081

Reaction notes

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