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(2S)-2-amino-2-phenylpropanoic acid → (S)-2-(Boc-amino)-2-phenylpropanoic acid

HRID 875151
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 875151
[C:1]1([C@:7]([C:10]([OH:12])=[O:11])([CH3:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].C[NH+](C)C.[C:18]([O:22][C:23](=O)[O:24]C(C)(C)C)([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[C:18]([O:22][C:23]([NH:8][C@@:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:10]([OH:12])=[O:11])[CH3:9])=[O:24])([CH3:21])([CH3:20])[CH3:19]
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Komponenten

5

Edukt 3

HCID 853461(2S)-2-amino-2-phenylpropanoic acidHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 11446287Trimethylazanium hydroxide

Produkt 1

HCID 13678038(S)-2-(Boc-amino)-2-phenylpropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 500 mg of 2-phenyl-D-alanine (3.02 mmol) and trimethylammonium hydroxide (aqueous solution 10%, 2.8 mL, 3.02 mmol) in 15 mL of acetonitrile, diterbutylcarbonate (1.047 g, 4.8 mmol) was added and the mixture was stirred at room temperature for 2 days. The solvent was then removed under vacuo, the residue was dissolved in water and washed with diethylether. The aqueous layer was acidified to pH=3-4 with citric acid and the product was extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with water, dried over Na2SO4 and evaporated. The title product was recovered as white solid (630 mg, yield 78%).

Aufarbeitung

  1. additionwas added
  2. customThe solvent was then removed under vacuo
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethylether
  5. extractionthe product was extracted with ethyl acetate (3×20 mL)
  6. washThe combined organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c0afb4300a946d18ec2bcf1e7e38b26
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08981089B2

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