Trifluoroacetic acid → (6-methyl-2-pyridinyl)acetic acid TFA salt

HRID 1910060노트

반응식

HRID 1910060 반응식
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])[CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>ClCCl>[OH:29][C:23]([C:25]([F:28])([F:27])[F:26])=[O:24].[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59341204Tert-butyl 2-(6-methylpyridin-2-yl)acetate

생성물 1

HCID 66823699(6-methyl-2-pyridinyl)acetic acid TFA salt수율 84.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,1-dimethylethyl (6-methyl-2-pyridinyl)acetate (711 mg, 3.43 mmol), triethylsilane (1.370 mL, 8.58 mmol) in Dichloromethane (DCM) (10 mL) was added TFA (3.44 mL, 44.6 mmol) dropwise via syringe. The reaction was stirred for overnight at room temperature. LCMS indicated good conversion, so the reaction was concentrated to a colourless oil, and diethyl ether (6 mL) was added. A white precipitate formed which was collected by filtration, dried at the pump for 10 mins, then under high-vacuum to afford (6-methyl-2-pyridinyl)acetic acid TFA salt (771 mg) as a white solid. LC-MS (ES) m/z=152 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.62 (s, 3H), 3.95 (s, 2H), 7.54 (d, J=7.33 Hz, 2H), 8.11 (br. s., 1H).

후처리

  1. concentrationso the reaction was concentrated to a colourless oil, and diethyl ether (6 mL)
  2. additionwas added
  3. customA white precipitate formed which
  4. filtrationwas collected by filtration
  5. customdried at the pump for 10 mins

출처 및 근거

ORD 기록
ord-a6615cdb13364fe48a28fcdd62d3eb1d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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