Methanesulfonic Acid → N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfinyl)acetamide

HRID 52115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52115
CS(O)(=O)=[O:3].[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:34])[CH2:26][S:27][CH2:28][CH2:29][O:30][C:31](=[O:33])[CH3:32])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.ClC1C=C(C=CC=1)C(OO)=O>ClCCCl>[N:6]1([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][NH:24][C:25](=[O:34])[CH2:26][S:27]([CH2:28][CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:3])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 70297m-Chloroperbenzoic acidHCID 9802303N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide

Produkt 1

HCID 67726274N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylsulfinyl)acetamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

77 μl of methanesulfonic acid was added to a solution of 0.50 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-acetoxyethylthio)acetamide (prepared as described in Example 2) in 5.5 ml of 1,2-dichloroethane, and the resulting mixture was cooled to -10° C. 0.28 g of 3-chloroperoxybenzoic acid (purity: 80%) was then added, and the reaction mixture was stirred, whilst keeping the temperature in the range from -10° C. to -5° C., for 2 hours. At the end of this time, it was washed with a 10% w/v aqueous solution of sodium hydrogensulfite, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of ethanol and chloroform as the eluent, to give 0.38 g (yield 73%) of the title compound as an oil.

Aufarbeitung

  1. customfrom -10° C. to -5° C.
  2. washAt the end of this time, it was washed with a 10% w/v aqueous solution of sodium hydrogensulfite, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customthe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethanol and chloroform as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-7b0c9d7ed6454b30a752554768608dc5
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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