Acetic Acid → Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylate

HRID 1629804노트

반응식

HRID 1629804 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]([CH3:23])([CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:5])#[N:2].O.[OH-].[Li+].CC(O)=O>C1COCC1.O.CCOC(C)=O>[C:1]([C:3]1[C:4](=[O:5])[NH:6][C:7]([CH3:23])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[N:2]

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86685897Ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate

생성물 1

HCID 86685898Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylate수율 115.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Intermediate 108A (1.2837 g, 4.06 mmol) was dissolved in a mixture of THF (15 mL) and water (3.00 mL) in a 25 mL 1 neck pear shaped flask that was equipped with a magnetic stirrer. Lithium hydroxide monohydrate (0.204 g, 4.87 mmol) was added and the reaction mixture was stirred at rt for 1 h. The reaction mixture was acidified to pH 4 with AcOH, diluted with EtOAc (50 mL) and the solution was washed with water (20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the desired product (1.40 g, 115%) as yellow oil. LCMS Anal. Calc'd for C17H18N2O3 298.1, found [M+H] 299.1.

후처리

  1. customwas equipped with a magnetic stirrer
  2. washthe solution was washed with water (20 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-80e00916ceb048edaf66008081cb30b3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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