Ammonium Hydroxide → HCID 11340480, Verbindung

HRID 602780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602780
C[O:2][C:3]([C:5]1[N:9]=[C:8]([C:10]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)[F:11])[O:7][N:6]=1)=O.[OH-].[NH4+:35]>CCO>[C:28]1([S:25]([C:10]([CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)([F:11])[C:8]2[O:7][N:6]=[C:5]([C:3]([NH2:35])=[O:2])[N:9]=2)(=[O:27])=[O:26])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 11317811HCID 11317811, Verbindung

Produkt 1

HCID 11340480HCID 11340480, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 70 mg (0.14 mmol) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid methyl ester in 3 mL of EtOH, were added 0.5 mL of an ammonium hydroxide solution (25% in water) and stirred over night. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over Na2SO4, filtered and evaporated. Recrystallisation in Et2O afforded 60 mg (86%) of (RS,SR)-5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazole-3-carboxylic acid amide as a light orange crystals, MS: 475 (MH+).

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customRecrystallisation in Et2O

Quellen und Nachweise

ORD-Eintrag
ord-cc84dd5725e44347adf2f86c5187de35
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906546B2

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