Sucrose → 1-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic Acid Ethyl Ester

HRID 1893035

Reaktionsgleichung

Reaktionsgleichung von HRID 1893035
C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[CH2:24]([O:26][C:27]([CH:29]1[C:33](=[O:34])[CH2:32][N:31]([C:35](=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH2:30]1)=[O:28])[CH3:25]>O>[CH2:24]([O:26][C:27]([CH:29]1[CH:33]([OH:34])[CH2:32][N:31]([C:35](=[O:52])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43])[CH2:30]1)=[O:28])[CH3:25]

Komponenten

4

Edukt 2

HCID 5988Sucrose2×HCID 686373971-(6-Benzyloxycarbonylamino-hexanoyl)-4-oxo-pyrrolidine-3-carboxylic Acid Ethyl Ester

Produkt 1

HCID 686374701-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic Acid Ethyl EsterAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
32 °C

Versuchsvorschrift

To a solution of sucrose (3 g) in distilled water (40 mL) was added Baker's yeast (2 g). The suspension was heated at 32° C. for 1 h. The content of the flask was then poured into a flask containing ketoester 60 (4 g, 9.88 mmol, dissolved in 4 mL of methanol). Stirring was continued at 32° C. for 24 h after which additional sucrose (3 g) in warm (40° C.) distilled water was added. After 48 h, the suspension was filtered through a pad of Celite. The pad was washed with water and the aqueous layer was extracted with ethyl acetate (3×250 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to flash chromatography (30% EtOAc/Hexane) to afford alcohol 62 (1.7 g, 42%).

Aufarbeitung

  1. additionThe content of the flask was then poured into a flask
  2. distillationdistilled water
  3. additionwas added
  4. waitAfter 48 h
  5. filtrationthe suspension was filtered through a pad of Celite
  6. washThe pad was washed with water
  7. extractionthe aqueous layer was extracted with ethyl acetate (3×250 mL)
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dea45f3e069c436291a07270579afd8d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507661B2

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