Octanoic Acid → HCID 14393357, Verbindung

HRID 1612912

Reaktionsgleichung

Reaktionsgleichung von HRID 1612912
[O:1]([CH2:13][CH3:14])[CH:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:15](O)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CCCCCC.C1C(CCCCC(N)=O)SSC1>[C:15]([O:12][CH2:11][C@H:9]1[O:10][CH:2]([O:1][CH2:13][CH3:14])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 2

HCID 379Octanoic AcidHCID 11127487Ethyl D-glucopyranoside

Produkt 1

HCID 14393357HCID 14393357, VerbindungAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 863LipoamideKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a suspension of ethyl D-glucopyranoside (500 g, 2.4 mol prepared according to example 10) and octanoic acid (520 g, 3.6 mol) in hexane (1000 ml) in a stirred batch reactor at 70° C. (reflux) was added immobilized lipase (5 g Lipozyme™, commercial available NOVO lipase prepared from a Mucor Miehei). Stirring was continued and the produced water was removed by azeotropic distillation. The progress of the reaction was followed by HPLC. As the product was being formed, the suspension gradually became a homogeneous solution (after 12 hours). After 52 hours the enzyme was removed by filtration and the solvent removed in vacuo. Excess fatty acid was removed by repeated molecular distillation giving a crude product (790 g, 91% monoester, 8% diester and 1% ethyl D-glucopyranoside). H1 and 13C NMR-spectra of the purified product were in accordance with the spectra for the pure α- and β-anomers given in tables 4 a/4 b.

Aufarbeitung

  1. temperature(reflux)
  2. customprepared from a Mucor Miehei)
  3. customthe produced water was removed by azeotropic distillation
  4. customAs the product was being formed
  5. customa homogeneous solution (after 12 hours)
  6. customAfter 52 hours the enzyme was removed by filtration
  7. customthe solvent removed in vacuo
  8. customExcess fatty acid was removed
  9. distillationdistillation

Quellen und Nachweise

ORD-Eintrag
ord-6d23595f3ed34f57b0bc6fbbe2de13b3
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05191071

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