4-Toluenesulfonyl chloride → HCID 59226402, Verbindung

HRID 73592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73592
[OH:1][CH2:2][C@@H:3]1[CH:7]([CH:8]([CH3:11])[CH2:9][OH:10])[O:6][C:5](=[O:12])[NH:4]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.CCO[C:27]([CH3:29])=O>N1C=CC=CC=1>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:10][CH2:9][CH:8]([CH:7]2[O:6][C:5](=[O:12])[NH:4][C@@H:3]2[CH2:2][O:1][S:19]([C:27]2[CH:29]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH3:11])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 59226593(4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one

Produkt 1

HCID 59226402HCID 59226402, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of (4R)-4-(hydroxymethyl)-5-(1-hydroxypropan-2-yl)oxazolidin-2-one (1.0 equiv.) in pyridine (0.15 M) at 0° C. was added p-toluenesulfonylchloride (2.1 equiv.). The solution was allowed to warm to rt as it stirred for 14 hours, at which time EtOAc was added and the solution was washed with H2O (3×), CuSO4(sat.) (2×), H2O, Na2CO3(sat.) and NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by silica gel chromatography (75% EtOAc/hexanes eluant) yielding 2-((4R)-2-oxo-4-(tosyloxymethyl)oxazolidin-5-yl)propyl 4-methylbenzenesulfonate (68%). LCMS (m/z): 484.1 (MH+); LC Rt=4.06 min.

Aufarbeitung

  1. additionwas added
  2. washthe solution was washed with H2O (3×), CuSO4(sat.) (2×), H2O, Na2CO3(sat.) and NaCl(sat.)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (75% EtOAc/hexanes eluant)

Quellen und Nachweise

ORD-Eintrag
ord-2155906fac214e1ea30417c84f971051
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829193B2

Notizen zur Reaktion

Wird geladen…