Acetic Anhydride → N-Acetyl-L-proline

HRID 487073

Reaktionsgleichung

Reaktionsgleichung von HRID 487073
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](OC(=O)C)(=[O:11])[CH3:10]>N1C=CC=CC=1>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 145742L-Proline

Produkt 1

HCID 66141N-Acetyl-L-prolineAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of L-Pro (247 mg, 2.15 mmol) in pyridine (1 ml) was added acetic anhydride (I ml), and the mixture was stirred at room temperature for 5 min. The solvent was removed in vacuo and the resulting oil was partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was dried over sodium sulfate, and concentrated, and the resulting solid was recrystallized from ethyl acetate to give N-acetyl-L-proline (167 mg, 44%), a white powder: m.p. 108° C. [lit 115° C. (from CHCl3)99 ]; [α]D25 -171° (c, 0.91, CHCl3) [(lit107 -118° (c, 1, H2O)] Anal. Calcd. for C7H11NO3 : C, 53.49; H, 7.05, N, 8.91. Found: C, 53.57; H, 7.09; N, 8.76.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe resulting oil was partitioned between ethyl acetate and 1N hydrochloric acid
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe resulting solid was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7e3aaae89ad547299f6feb8befed11a8
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294603

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