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Water → HCID 25134321, Verbindung

HRID 1970929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1970929
[CH3:1][CH2:2][C@@H:3]([CH:28]([CH3:30])[CH3:29])/[CH:4]=[CH:5]/[C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7].CS(N)(=O)=[O:33].[K].C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)[O-].[Na+].[OH2:49]>C(O)(C)(C)C>[OH:49][C@@H:5]([C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)[CH3:7])[C@@H:4]([OH:33])[C@H:3]([CH:28]([CH3:29])[CH3:30])[CH2:2][CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 962WaterHCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 516919Sodium BisulfateHCID 5462222PotassiumHCID 6442194Stigmasta-4,22-Dien-3-One

Produkt 1

HCID 25134321
HCID 25134321, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

420 mg of (22E)-stigmasta-4,22-dien-3-one are dissolved in 100 mL of tert-butanol and the same volume of water is added. To this mixture 0.93 g of the chiral auxiliary DHQD2-Phal, 450 mg (2 mmol) methanesulphonamide, 4.5 g of potassium ferricianide, 2 g of potassium carbonate and 30 mg de potassium osmate are added. The mixture is vigorously stirred, at ambient temperature, during 9 days. The reaction, controlled by thin layer chromatography is not completed. Little portions of solid sodium bisulphate are added, until bubbling stops. The mixture is extracted with ethyl acetate, washed with 0.25M aqueous sulphuric acid, then with 10% NaOH 10%, and finally with water. The organic phase is dried and evaporated. The crude product is purified by column chromatography (eluting solvent: hexane/ethyl acetate 1:1). 180 mg of (22S,23S)-22,23-dihydroxystigmast-4-en-3-one are obtained, subsequently 165 mg of (22R,23R)-22,23-dihydroxystigmast-4-en-3-one are eluted.

Aufarbeitung

  1. customThe reaction
  2. customuntil bubbling stops
  3. extractionThe mixture is extracted with ethyl acetate
  4. washwashed with 0.25M aqueous sulphuric acid
  5. customThe organic phase is dried
  6. customevaporated
  7. customThe crude product is purified by column chromatography (eluting solvent: hexane/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c47722fc09cf409ba0c698eea4bb6a81
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08431554B2

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