Ammonium Hydroxide → 3-(Aminosulphonyl)benzeneboronic acid

HRID 1927962Notes

Reaction equation

HRID 1927962 reaction equation
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]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 31398ChlorosuccinimideHCID 68690790HCID 68690790, compound

Product 1

HCID 441193233-(Aminosulphonyl)benzeneboronic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)−].

Workup

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

Sources & evidence

ORD record
ord-065720fb7591472f80842e4133df0ffb
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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