Ammonium Hydroxide → 3-(Aminosulphonyl)benzeneboronic acid

HRID 1927962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927962
Cl[N:2]1C(=O)CCC1=O.CN1CC[O:15][B:14]([C:18]2[CH:19]=[C:20]([S:24]([O-:26])=[O:25])[CH:21]=[CH:22][CH:23]=2)[O:13]CC1.[Li+].[OH-].[NH4+]>C(Cl)Cl>[S:24]([C:20]1[CH:19]=[C:18]([B:14]([OH:15])[OH:13])[CH:23]=[CH:22][CH:21]=1)(=[O:26])(=[O:25])[NH2:2]

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 31398ChlorosuccinimideHCID 68690790HCID 68690790, Verbindung

Produkt 1

HCID 441193233-(Aminosulphonyl)benzeneboronic acidAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Step 2) N-Chlorosuccinimide (1.015 g, 7.6 mmol) was added to a suspension of the above prepared lithium 3-(6-methyl-[1,3,6,2]dioxazaborocan-2-yl)-benzenesulfinate (2 g, 7.27 mmol) in CH2Cl2 (14 mL) and the mixture was stirred for 2 h at rt.Ai solution of 25% ammonium hydroxide (1.09 mL, 14.5 mmol) was added and the mixture was stirred again for 2 h at rt, then completely evaporated to give the title compound as an off-white solid (1.38 g, 94%) (according to Bioorg. Med. Chem. 2005, 13, 2305-2312). MS (ISP) 200.4 [(M−H)−].

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred again for 2 h at rt
  3. customcompletely evaporated

Quellen und Nachweise

ORD-Eintrag
ord-065720fb7591472f80842e4133df0ffb
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183262B2

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