Pyridine → HCID 58503128, Verbindung

HRID 1949609

Reaktionsgleichung

Reaktionsgleichung von HRID 1949609
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C@H:14]([OH:18])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.CN(C1C=CN=CC=1)C>[C:25]([O:18][C@@H:14]([CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:15]([OH:17])=[O:16])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 2733930(S)-2-Hydroxy-4-(((phenylmethoxy)carbonyl)amino)butyric acid

Produkt 1

HCID 58503128HCID 58503128, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of (S)-4-(benzyloxycarbonylamino)-2-hydroxybutanoic acid (1, 612 g, 2.41 mol) in THF (6 L) at 0° C. was added DMAP (2.4 g) and pyridine (196 mL, 2.41 mol). After stirring for 20 minutes, benzoyl chloride (280 mL) was added slowly and the reaction was allowed to stir overnight at room temperature. The resulting precipitate was filtered and the filtrate was acidified with 1 M citric acid (1 L). The organic solvent was removed by rotary evaporation and the desired product was extracted with EtOAc (2×2 L). The combined organic layers were washed with 1 M citric acid (1 L), brine (1 L) and then dried over MgSO4. Solvent removal under vacuum resulted in a viscous oil, which was purified on a 6-inch reverse-phase HPLC column to yield (S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid (2) as a non-flowing viscous oil (439 g, 51% yield).

Aufarbeitung

  1. stirringto stir overnight at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. customThe organic solvent was removed by rotary evaporation
  4. extractionthe desired product was extracted with EtOAc (2×2 L)
  5. washThe combined organic layers were washed with 1 M citric acid (1 L), brine (1 L)
  6. dry with materialdried over MgSO4
  7. customSolvent removal under vacuum
  8. customresulted in a viscous oil, which
  9. customwas purified on a 6-inch reverse-phase HPLC column

Quellen und Nachweise

ORD-Eintrag
ord-d93126a2f8ba42a28863f775dba045ff
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399419B2

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