Benzoyl chloride → (S)-3-(Benzoylaminomethyl)-5-methylhexanoic acid

HRID 48537

Reaktionsgleichung

Reaktionsgleichung von HRID 48537
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH2:13][C@H:14]([CH2:19][NH2:20])[CH2:15][C:16]([OH:18])=[O:17])[CH3:12]>C1COCC1>[C:1]([NH:20][CH2:19][C@@H:14]([CH2:13][CH:11]([CH3:12])[CH3:10])[CH2:15][C:16]([OH:18])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 5486971Pregabalin

Produkt 1

HCID 9813903(S)-3-(Benzoylaminomethyl)-5-methylhexanoic acidAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Benzoyl chloride (0.88 ml, 7.6 mmol) was added to a stirred suspension of pregabalin (1.0 g, 6.3 mmol) in THF (80 ml) at room temperature under argon and the reaction mixture was stirred for 18 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was chromatographed (SiO2, heptane-ethyl acetate, 1:1 to 3:7) to give 4 (0.78 g, 47%).

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed (SiO2, heptane-ethyl acetate, 1:1 to 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-9eada8501a9241f8bf39909cddae410d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703522B2

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