Chromic Acid → N-Carbobenzyloxy-4-keto-L-proline

HRID 848446

Reaktionsgleichung

Reaktionsgleichung von HRID 848446
[C:1]([N:11]1[CH2:18][CH:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Cr](O)(O)(=O)=O>CC(C)=O.S(=O)(=O)(O)O>[C:1]([N:11]1[CH2:18][C:17](=[O:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

5

Edukt 2

HCID 24425Chromic AcidHCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 11076282N-Carbobenzyloxy-4-keto-L-prolineAusbeute 10,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

21.5 g. (0.81 mole) of N-carbobenzyloxy-4-hydroxy-L-proline is oxidized in 1.2 liters of acetone with 83 ml. of 8 N chromic acid in sulfuric acid as described in J.A.C.S.79, 189 (l957). In order to facilitate the subsequent filtration of chromium salts, 30 g. of Celite (diatomaceous earth) is added to the acetone solution before introduction of the oxidizing agent. An air stirrer is employed. The reaction mixture is filtered and the acetone filtrate is concentrated to approximately 300 ml. before diluting with 1 liter of chloroform. The solution is washed with 300 ml. of saturated sodium chloride (four times), dried (MgSO4), filtered and the solvent evaporated to give N-carbobenzyloxy-4-keto-L-proline (22.8 g.) which is crystallized from ether (50 ml.)-hexane (150 ml.) to obtain 17.2 g. (81%) of product, m.p. 99°-101°, [α]D26 +17° (c, 1% in chloroform).

Aufarbeitung

  1. filtrationthe subsequent filtration of chromium salts, 30 g
  2. additionof Celite (diatomaceous earth) is added to the acetone solution before introduction of the oxidizing agent
  3. customAn air stirrer is employed
  4. filtrationThe reaction mixture is filtered
  5. concentrationthe acetone filtrate is concentrated to approximately 300 ml
  6. additionbefore diluting with 1 liter of chloroform
  7. washThe solution is washed with 300 ml
  8. dry with materialof saturated sodium chloride (four times), dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b4461bb6bb16476f91ec5180928dc8ec
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04296113

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