Potassium Carbonate → Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate

HRID 525997ノート

反応式

HRID 525997 の反応式
[O:1]=[C:2]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][N:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+]>CO>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:2](=[O:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N:11][CH:12]=1)#[CH:17]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 89444199Methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate

生成物 1

HCID 89443928Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate収率 60%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate (26 mg, 0.085 mmol) in methanol, potassium carbonate (5.90 mg, 0.042 mmol) is added in one portion and the reaction mixture is stirred at room temperature for 2 h. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was dried on magnesium sulfate and concentrated under vacuum to give methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate A41 (12 mg, 60% yield). 1H NMR (400 MHz, CDCl3) 8.39 (d, 1H), 8.16 (m, 2H), 7.77 (d, 1H), 3.72 (s, 3H), 2.74 (m, 4H) ppm.

後処理

  1. customthe solution was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. customThe combined organic layer was dried on magnesium sulfate
  5. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-511d2a41211c4fe792dc6bbe6036081d
出典データセット
uspto-grants-2016_05
特許番号
US09345244B2

反応ノート

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