Hydrogen Peroxide → Modafinil acid

HRID 230767

Reaktionsgleichung

Reaktionsgleichung von HRID 230767
[CH:1](CC(O)=S)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[S:19]([OH:22])(=O)=O.[OH:23]O.[CH:25]([OH:28])([CH3:27])C>CO.O.OS([O-])=O.[Na+]>[CH:1]([S:19]([CH2:27][C:25]([OH:28])=[O:23])=[O:22])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

8

Edukt 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 178526172HCID 178526172, Verbindung

Produkt 1

HCID 3085267Modafinil acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 23665763Sodium BisulfiteLösungsmittel

Versuchsvorschrift

To a suspension of benzhydrylthioacetic acid (63.7 g, 0.246 mol) in methanol (250 mL) was added a solution of concentrated H2SO4 (1.6 mL) in isopropyl alcohol (65 mL) at room temperature (about 22 degrees C.). To this suspension was added 30% H2O2 in water (65 mL) drop wise over 25 minutes. The reaction was monitored by TLC and was completed within 2 hours. The solution was diluted with a solution of NaHSO3 (125 mg) in water (700 mL). The resulting precipitate was filtered, washed with water, then methanol: water (1:1), and dried to give benzhydrylsulfinylacetic acid (47.6 g). 1H-NMR indicated the desired product was obtained along with ˜10 percent starting material and some impurities. The compound was triturated with ethanol (100 mL), filtered and dried to give pure benzhydrylsulfinylacetic acid (33.4 g, 49.4%) as a colorless solid. (See Prisinzano, T. et al, Tetrahedron Asymm., 2004, 15, 1053-1058)

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. dry with materialmethanol: water (1:1), and dried

Quellen und Nachweise

ORD-Eintrag
ord-6935a4be591a4b9f84caccdc8c07e2c5
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566805B2

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