Methanol → Methyl 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate

HRID 1399731ノート

反応式

HRID 1399731 の反応式
S(Cl)(Cl)=O.[O:5]=[C:6]1[NH:11][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:9][C:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]1[CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([OH:27])=[O:26].[CH3:31]O>>[O:5]=[C:6]1[NH:11][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:9][C:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:7]1[CH:24]([CH2:28][CH2:29][CH3:30])[C:25]([O:27][CH3:31])=[O:26]

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1363461692-(6-Oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

生成物 1

HCID 136346149Methyl 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate

実験手順

To a solution cold solution of methanol (20 mL) was added thionyl chloride (2.90 mL; 40 mmol) dropwise. The acidic solution was added to a flask containing 2-(6-oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid (1.67 g; 4.71 mmol) and the mixture was heated to reflux for 18 h. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water and neutralized with a saturated solution of sodium hydrogen carbonate. The suspension was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The product was used as such in the next reaction.

後処理

  1. additionThe acidic solution was added to a flask
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 18 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in water
  6. extractionThe suspension was extracted twice with ethyl acetate
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customsuch in the next reaction

出典と根拠

ORDレコード
ord-d576a46462ba4d6288823c8938d4e4a5
出典データセット
uspto-grants-2014_12
特許番号
US08906906B2

反応ノート

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