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Hydrochloric Acid → Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

HRID 1272430
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1272430
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:38]C)=[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][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(=[O:11])=[O:10])[CH:8]=1)#[N:2].[Cl-].[Li+].C(OCC)(=O)C.Cl>CN(C)C=O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:38])=[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][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(=[O:10])=[O:11])[CH:8]=1)#[N:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 10393283Ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetate

Produkt 1

HCID 12149205Ethyl[4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2'-methanesulfonyl-biphenyl-3-yloxy]acetateAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of 4.62 g of ethyl [4-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate in 40 mL of N,N-dimethylformamide was added 1.03 g of lithium chloride, and the mixture was stirred at 140° C for 2 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of 60 mL of ethyl acetate, 6 mL of toluene, and 32 mL of 1 mol/L hydrochloric acid. The organic layer was separated, and washed with 1 mol/L hydrochloric acid and brine. The organic layer was 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: acetic acid-ethyl acetate) to give 3.67 g of ethyl [4-[2-(5-cyano-2-hydroxybenzenesulfonylamino)ethyl]-2′-methanesulfonyl-biphenyl-3-yloxy]acetate, colorless and amorphous.

Aufarbeitung

  1. temperatureAfter being cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with 1 mol/L hydrochloric acid and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: acetic acid-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5e098b3b5e1542688d9e07effb42623e
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07208524B2

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