Ethyl Acetate → (+/-)-(3-Fluoro-4-((2,2,2-trifluoro-1-phenylethyl)carbamoyl)phenyl)boronic acid

HRID 595792

反応式

HRID 595792 の反応式
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].CN(C)C(=C(C)C)C.[F:22][C:23]([F:33])([F:32])[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:25].CCOC(C)=O>C(Cl)Cl>[F:13][C:6]1[CH:5]=[C:4]([B:1]([OH:2])[OH:3])[CH:12]=[CH:11][C:7]=1[C:8](=[O:10])[NH:25][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23]([F:22])([F:32])[F:33]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 89166alpha-(Trifluoromethyl)benzenemethanamineHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 15569623HCID 15569623、化合物

生成物 1

HCID 123606597(+/-)-(3-Fluoro-4-((2,2,2-trifluoro-1-phenylethyl)carbamoyl)phenyl)boronic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A mixture of 4-borono-2-fluorobenzoic acid (54 mg, 0.294 mmol) in DCM (1468 μL) was cooled to 0° C. Then ghosez reagent N,N,3-trimethylbut-2-en-2-amine (65.8 μL, 0.587 mmol) was added and the whole mixture was stirred at rt for 20 min. The mixture was added into a mixture of TEA (246 μL, 1.762 mmol), 2,2,2-trifluoro-1-phenylethanamine (59.1 mg, 0.338 mmol) and DCM (1468 μL). The reaction was stirred at room temperature for 2 h. To the reaction mixture was added EtOAc, and washed with sat. sodium bicarbonate, water, and dried over Na2SO4. Filtered and concentrated to provide the crude product which was taken to the next step without further purification. LCMS (m/z): 342.2 (MH+), 0.84 min.

後処理

  1. additionwas added
  2. stirringThe reaction was stirred at room temperature for 2 h
  3. washwashed with sat. sodium bicarbonate, water
  4. dry with materialdried over Na2SO4
  5. filtrationFiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-49a1d99c282d4e52924273ca614f866f
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

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