Hydrochloric Acid → (2S)-1-benzoylpyrrolidine-2-carboxylic acid

HRID 1756040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756040
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>[OH-].[Na+]>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 145742L-Proline

Produkt 1

HCID 6988239(2S)-1-benzoylpyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

To a well-stirred solution of L-proline (5.75 g, 0.05 mmole) in 2N NaOH (25 ml), 4N NaOH (12.5 ml) and benzoyl chloride (5.8 ml, 0.05 mole) were added dropwise from different drop funnels, maintaining the temperature near 0°-4° C. The mixture after 15 minutes was acidified with 1N HCl. The resulting oil was extracted with CHCl3, the combined organic extract was dried (MgSO4), and the solvent was removed. Ether was added to the residue and the mixture was allowed to stand overnight at 0° C. The crystals of N-benzoyl-L-proline were separated. Yield 3.42 g (60%), m.p. 152°-154° C., [α]D20 -68.5° (c 0.4; CHCl3); Rf 0.13 (Kiesel-gel, CHCl3 --CH3OH, 9:1). Analysis Calcd. for C12H13NO3 : C, 65.73; H, 5.99; N, 6.39. Found: C, 65.64; H, 6.03; N, 6.54.

Aufarbeitung

  1. temperaturemaintaining the temperature near 0°-4° C
  2. extractionThe resulting oil was extracted with CHCl3
  3. extractionthe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. customthe solvent was removed
  6. additionEther was added to the residue
  7. customThe crystals of N-benzoyl-L-proline were separated

Quellen und Nachweise

ORD-Eintrag
ord-a7265a61893548c7b66523419f58e82a
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439930

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