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Sulfuryl chloride → (5R)-3-(4-(1-Isopropylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723799
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 723799
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1.C(=O)(O)[O-].[Na+].[CH:32]([S:35](Cl)(=[O:37])=[O:36])([CH3:34])[CH3:33].S(Cl)(Cl)(=O)=O>O.CC(C)=O>[CH:32]([S:35]([N:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1)(=[O:37])=[O:36])([CH3:34])[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24648Sulfuryl chlorideHCID 824082-Propanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69364214(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride

Produkt 1

HCID 69366716(5R)-3-(4-(1-Isopropylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one
Ausbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (380 mg, 1 mM) was dissolved in water (5 ml), which was then diluted with acetone (10 ml), and solid sodium bicarbonate (0.84 g, 10 mM) added. The mixture was stirred and cooled to 0° C., and isopropylsulfonyl chloride (285 mg, 2 mM) added dropwise. After stirring for 5 hours, an equal portion of sulfonyl chloride was added, and stirring continued for 18 hours. Most acetone was removed by evaporation, the residue diluted with water (50 ml), and extracted with ethyl acetate (3×20 ml). The extracts were washed with brine and dried (magnesium sulfate). The residual oil after evaporation was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (205 mg).

Aufarbeitung

  1. additionadded
  2. stirringAfter stirring for 5 hours
  3. stirringstirring
  4. customMost acetone was removed by evaporation
  5. additionthe residue diluted with water (50 ml)
  6. extractionextracted with ethyl acetate (3×20 ml)
  7. washThe extracts were washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. customThe residual oil after evaporation
  10. customwas purified by chromatography on a 10 g silica Mega Bond Elut® column
  11. washeluting with
  12. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  13. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-47e740d465ec44c3b8a2abaa00d76422
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07141583B2

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