tert-Butylsulfinamide, (R)-(+)- → (NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

HRID 1361188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361188
[CH3:1][S:2]([C:5]1[S:6][C:7]([C:10](=O)[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:20]\[S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3]

Komponenten

7

Edukt 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 592783971-(2-Methanesulfonyl-thiazol-5-yl)-propan-1-one

Produkt 1

HCID 87126692(NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11026Titanium isopropoxideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one (110 mg, 0.50 mmol), (R)-2-methyl-2-propanesulfinamide (70 mg, 0.6 mmol) and titanium (IV) isopropoxide (0.29 mL, 1.0 mmol) in THF (10 mL) was warmed at reflux for 18 hours. The mixture was cooled to room temperature and diluted with diethyl ether (100 mL) and water (6 mL). After 10 minutes with stirring, the solution was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide.

Aufarbeitung

  1. temperaturewas warmed
  2. temperatureat reflux for 18 hours
  3. dry with materialthe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of 0-100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-cfa7a60ab298436d9e2b4c03a749b674
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879873B2

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