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

HRID 595792

반응식

HRID 595792 반응식
[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]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 89166alpha-(Trifluoromethyl)benzenemethanamineHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 15569623HCID 15569623, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-49a1d99c282d4e52924273ca614f866f
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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