(R)-4-(Oxiran-2-ylmethoxy)benzonitrile → 4-[3-[ethyl[3-((S*)-propylsulfinyl)propyl]amino]-2(R)-hydroxypropoxy]-benzonitrile

HRID 1886000Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886000
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][S@:7]([CH2:9][CH2:10][CH3:11])=[O:8])[CH3:2].[O:12]1[CH2:14][C@@H:13]1[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1>C(O)(C)C>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][S@:7]([CH2:9][CH2:10][CH3:11])=[O:8])[CH2:14][C@@H:13]([OH:12])[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 6934186(R)-4-(Oxiran-2-ylmethoxy)benzonitrileHCID 86745130ethyl(3-(S*)-propylsulfinyl)propylamine

Produkt 1

HCID 545546274-[3-[ethyl[3-((S*)-propylsulfinyl)propyl]amino]-2(R)-hydroxypropoxy]-benzonitrileAusbeute 102,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 3 g of ethyl (3-(S*)-propylsulfinyl)propylamine and 3.18 g of (R)-4-(oxiranylmethoxy)benzonitrile was refluxed for 16 h in 25 ml of isopropyl alcohol. After evaporation of the solvent, the crude product was dissolved in 2M hydrochloric acid, washed with ether, the solution brought to pH 11.5 with 2M sodium hydroxide and extracted with dichloromethane. Evaporation of the organic phase gave 6.11 g of an oil,

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. dissolutionthe crude product was dissolved in 2M hydrochloric acid
  3. washwashed with ether
  4. extractionextracted with dichloromethane
  5. customEvaporation of the organic phase

Quellen und Nachweise

ORD-Eintrag
ord-2570ec08fc6a424cb420763d20033be4
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149523

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