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

HRID 525997노트

반응식

HRID 525997 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-511d2a41211c4fe792dc6bbe6036081d
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345244B2

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