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

HRID 423533노트

반응식

HRID 423533 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 44318944-Mercaptophenylboronic acid

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-cc96d83cf8c44c2f95e2db6ce75b7cac
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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