Hydrochloric Acid → 5-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

HRID 733360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 733360
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:35][CH3:36])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:17][C:16]=2[O:31]COC)(=[O:11])=[O:10])[CH:8]=1)#[N:2].Cl>C(O)(C)C.O1CCCC1.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:35][CH3:36])=[C:7]([S:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27]([CH3:30])(=[O:28])=[O:29])=[CH:17][C:16]=2[OH:31])(=[O:10])=[O:11])[CH:8]=1)#[N:2]

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 178562285-cyano-N-[2-(2'-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamide

Produkt 1

HCID 178562275-cyano-N-[2-(3-hydroxy-2'-methanesulfonylbiphenyl-4-yl)ethyl]-2-methoxybenzenesulfonamideAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 14.89 g of 5-cyano-N-[2-(2′-methanesulfonyl-3-methoxymethoxybiphenyl-4-yl)ethyl]-2-meth oxybenzenesulfonamide in a mixture of 30 mL of isopropanol and 90 mL of tetrahydrofuran was added 11.7 mL of concentrated hydrochloric acid. After being stirred at 50° C. for 2 hours, the reaction mixture was diluted with 50 mL of water, and extracted with 150 mL of ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-methanol) to give 10.22 g of 5-cyano-N-[2-(3-hydroxy-2′-methanesulfonylbiphenyl-4-yl)ethyl]-2-Methoxybenzenesulfonamide, colorless and amorphous.

Aufarbeitung

  1. extractionextracted with 150 mL of ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-fc4000476261471a9ad60ba1ba8acc1f
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589126B2

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