Sodium Hydroxide → L-Phenylalanine

HRID 1252362

Reaktionsgleichung

Reaktionsgleichung von HRID 1252362
[OH-].[Na+].C[O:4][C:5](=[O:18])[CH:6]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:7]C(=O)C>CCC(=O)CCCC>[NH2:7][C@H:6]([C:5]([OH:18])=[O:4])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 97805Methyl N-acetyl-DL-phenylalaninate

Produkt 1

HCID 6140L-Phenylalanine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 78023-HeptanoneLösungsmittel2×

Versuchsvorschrift

The aqueous layer obtained was adjusted to pH 8 by adding 1 N aqueous sodium hydroxide. To this aqueous layer was added a solution of 1 g of the N-acetyl-DL-phenylalanine methyl ester obtained in step (iv) of Example 3 in 5 ml of 3-heptanone. The resultant two-layer-system mixture was shaken in the same manner as above at a temperature of 37° C. for 12 hours (repeated reaction run No. 1). When the reaction was completed, the pH of the aqueous layer was 5.50. Upon cooling the reaction mixture composed of the aqueous layer and 3-heptanone layer to room temperature, a supersaturation portion (0.11 g) of L-phenylalanine precipitated out on the aqueous layer side. Crystals of L-phenylalanine were separated by filtration. Then the filtrate was allowed to separate into the aqueous layer and 3-heptanone layer and the organic layer was removed. The aqueous layer was subjected to pH adjustment (pH 8) and reaction with N-acetyl-DL-phenylalanine methyl ester in 3-heptanone solution with shaking in the same manner as mentioned above and the resultant crystalline L-phenylalalnine precipitate (0.15 g) was collected by filtration (repeated run No. 2). By using the aminoacylase-containing aqueous layer of the filtrate in the above manner, the overall procedure comprising pH adjustment, reaction and L-phenylalanine separation was further repeated. The yields of L-phenylalanine in repeated runs No. 3, No. 4 and No. 5 were 0.16 g, 0.13 g and 0.12 g, respectively. The L-phenylalanine crystals obtained in the above repeated runs Nos. 1-5 (0.67 g in total) were combined and washed with methanol. The optical purity of the L-phenylalanine after washing (0.65 g) was found to be 98.9 percent.

Aufarbeitung

  1. customThe aqueous layer obtained
  2. customreaction run No
  3. temperatureUpon cooling the reaction mixture
  4. customa supersaturation portion (0.11 g) of L-phenylalanine precipitated out on the aqueous layer side
  5. customCrystals of L-phenylalanine were separated by filtration
  6. customto separate into the aqueous layer and 3-heptanone layer
  7. customthe organic layer was removed
  8. customadjustment (pH 8) and reaction with N-acetyl-DL-phenylalanine methyl ester in 3-heptanone solution
  9. filtrationwas collected by filtration (
  10. customadjustment, reaction and L-phenylalanine separation

Quellen und Nachweise

ORD-Eintrag
ord-71e3911a27a144d3b6568601dbb0ca25
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743547

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