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

HRID 1910060ノート

反応式

HRID 1910060 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a6615cdb13364fe48a28fcdd62d3eb1d
出典データセット
uspto-grants-2013_12
特許番号
US08598156B2

反応ノート

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