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

HRID 853953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 853953
[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-methoxybenzenesulfonamide 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 as a colorless 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-1faf672977e641298e79bd5c704749e1
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256215B2

Notizen zur Reaktion

Wird geladen…