Sodium Hydroxide → Dl-Phenylalanine

HRID 1905818Notes

Reaction equation

HRID 1905818 reaction equation
[CH2:1]([CH:8]1[NH:12]C(=O)N[C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:15].[Na+]>O.CCOCCO>[NH2:12][CH:8]([C:9]([OH:14])=[O:15])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 735655-(Phenylmethyl)-2,4-imidazolidinedione

Product 1

HCID 994Dl-PhenylalanineYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

95.1 g (0.5 mole) of 5-benzyl-hydantoine are dissolved in a solution of 87 g of sodium hydroxide and 400 ml of water, whereupon 300 ml of cellosolve are added. The reaction mixture is heated to boiling for 48 hours, the water and the cellosolve are distilled off in vacuo (30 Hgmm, 80° C.), the solid residue is dissolved in a small amount of water and acidified with concentrated hydrochloric acid (pH 2). The solution is treated with activated charcoal and the pH is adjusted to 6 with a concentrated ammonium hydroxide solution. The mixture is allowed to stand for some hours at 5° C. The precipitated product is filtered off, washed with cold water and cold ethanol. Thus 63.4 g of the desired airdry compound are obtained, yield 77%, mp.: 245°-255° C. Purity: 97.9% according to HPLC.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. distillationthe water and the cellosolve are distilled off in vacuo (30 Hgmm, 80° C.)
  4. dissolutionthe solid residue is dissolved in a small amount of water
  5. additionThe solution is treated with activated charcoal
  6. waitto stand for some hours at 5° C
  7. filtrationThe precipitated product is filtered off
  8. washwashed with cold water and cold ethanol
  9. customThus 63.4 g of the desired airdry compound are obtained

Sources & evidence

ORD record
ord-0e0eba00edd64920878d55366b7c707a
Source dataset
uspto-grants-1987_03
Patent number
US04647694

Reaction notes

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