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Thionyl Chloride → Ethyl (4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide

HRID 249364
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 249364
[OH:1][C@@H:2]([C@H:8]([OH:25])[C:9](=[O:24])[NH:10][C@H:11]([C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[S:26](Cl)(Cl)=[O:27]>C(Cl)(Cl)(Cl)Cl>[CH3:14][CH:13]([CH3:15])[CH2:12][C@H:11]([NH:10][C:9]([C@H:8]1[O:25][S:26](=[O:27])[O:1][C@@H:2]1[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:24])[C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]
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Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 53688291Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate

Produkt 1

HCID 54321787Ethyl (4S,5S)-5-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-1,3,2-dioxathiolane-4-carboxylate-2-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Ethyl (2S,3S)-2,3-dihydroxy-3-[(S)-3-methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]propionate (305 mg) obtained in Example 2 was dissolved in carbon tetrachloride (6 ml). Thionyl chloride (69 μl) was added to the resultant solution at room temperature, and the solution was heated under reflux for 40 minutes. The reaction solution was condensed under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (a developing solvent; hexane:ethyl acetate=2:1) to obtain 174 mg of a target compound as white crystals. This product was a diastereomer mixture due to 2-position asymmetry. Therefore, the mixture was subjected to silica gel column chromatography again to obtain a high-polarity isomer (compound A) and a low-polarity isomer (compound B). NMR data and SIMS data of the compounds A and B were as follows.

Aufarbeitung

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 40 minutes
  3. customcondensed under reduced pressure
  4. customto obtain a crude product
  5. customThis crude product was purified by silica gel column chromatography (a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-b93afc47f42048fba747ad4e8d014764
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05214056

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