Phosphoric Acid → D-2-Amino-5-phenyl-pentanoic acid

HRID 650679Notes

Reaction equation

[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].P(=O)(O)(O)O>O>[NH2:1][C@H:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

(±)-2-Amino-5-phenylpentanoic acid (35 g, from Example 40a) was suspended in water (3 L) and solubilized by adjust the pH to 12 with 7 N NaOH solution. The pH was readjusted to pH 8 with 1 M phosphoric acid while stiirng at 45° C. The solution was cooled to 40° C., and L-amino acid oxidase (Sigma, 0.7 unit/mg) was added. The reaction was stirred with good aeration for 2 weeks. The reaction mixture was concentrated to 500 mL under vacuum, the pH was adjusted to 5, and the precipitate was collected. The material was recrystallized from ethanol-water to afford 17.32 g of the title compound).

Workup

customwhile stiirng at 45° C
concentrationThe reaction mixture was concentrated to 500 mL under vacuum
customthe precipitate was collected
customThe material was recrystallized from ethanol-water

Sources & evidence

ORD record: ord-af8b33b0af7c41ad904f62e64c12bd5b
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274715B1

Reaction notes

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