Potassium Carbonate → {4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acid

HRID 423533ノート

反応式

HRID 423533 の反応式
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([NH2:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:15][C:13](=[O:14])[CH2:12][S:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 44318944-Mercaptophenylboronic acid

生成物 1

HCID 66673418{4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acid収率 49%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 2-bromoacetamide (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.6 g (49%) of {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid as a white solid. The boronic acid was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 2H), 7.68 (d, 2H, J=8.2 Hz), 7.55 (bs, 1H), 7.24 (d, 2H, J=8.2 Hz), 7.15 (bs, 1H), 3.61 (s, 2H); LRMS (APCI), m/z 210 (M−H).

後処理

  1. customAfter CH3CN was removed
  2. additionwater was added to the residue
  3. filtrationthe solid was collected via filtration
  4. washwashed with water

出典と根拠

ORDレコード
ord-cc96d83cf8c44c2f95e2db6ce75b7cac
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

反応ノート

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