Dichloromethane → HCID 23311271、化合物

HRID 746029

反応式

HRID 746029 の反応式
[CH3:1][C:2]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]([CH2:21][C@H:22]([NH2:26])[C:23]([OH:25])=O)=[O:20])=[CH:13][CH:12]=1.Cl[CH2:28]Cl>C(N(CC)CC)C>[CH3:1][C:2]1([C:8]([NH:26][CH:22]([C:23](=[O:25])[CH3:28])[CH2:21][C:19]([O:18][CH2:17][C:14]2[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=2)=[O:20])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 1011864-(Phenylmethyl) hydrogen L-aspartateHCID 41892451-Methylcyclohexanecarbonyl chloride

生成物 1

HCID 23311271HCID 23311271、化合物

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

1-Methylcyclohexylcarbonyl chloride (1.6 g) was added dropwise to a mixture of L-aspartic acid β-benzyl ester (2.23 g), dichloromethane (30 ml) and triethylamine (30 ml) with ice-cooling and stirring. The resulting mixture was stirred with ice-cooling for an hour, washed with 1N hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the oily residue (3.2 g) was dissolved in dimethoxyethane (30 ml). Acetic anhydride (4 ml), pyridine (4.8 ml) and 4-dimethylaminopyridine (0.12 g) were added and the mixture was refluxed for 1.5 hours. Acetic acid (2 ml) was added and the whole mixture was refluxed for 2.5 hours. The solvent was distilled off and water was added. The mixture was extracted with ethyl acetate and the ethyl acetate layer was washed with diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate and water in that order, and dried over anhydrous magnesium sulfate. The residue (2.0 g) was purified by chromatography on silica gel (40 g) [eluent: hexane-acetone (9:1)] to give benzyl 3-(1-methylcyclohexylcarbonylamino)-4-oxovalerate as an oil; yield 1.2 g (34.8%).

後処理

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred with ice-
  3. temperaturecooling for an hour
  4. washwashed with 1N hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. dissolutionthe oily residue (3.2 g) was dissolved in dimethoxyethane (30 ml)
  8. additionAcetic anhydride (4 ml), pyridine (4.8 ml) and 4-dimethylaminopyridine (0.12 g) were added
  9. temperaturethe mixture was refluxed for 1.5 hours
  10. additionAcetic acid (2 ml) was added
  11. temperaturethe whole mixture was refluxed for 2.5 hours
  12. distillationThe solvent was distilled off
  13. additionwater was added
  14. extractionThe mixture was extracted with ethyl acetate
  15. washthe ethyl acetate layer was washed with diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate and water in that order
  16. dry with materialdried over anhydrous magnesium sulfate
  17. customThe residue (2.0 g) was purified by chromatography on silica gel (40 g) [eluent: hexane-acetone (9:1)]

出典と根拠

ORDレコード
ord-488c54a181064787bca5de4a469968e7
出典データセット
uspto-grants-1986_07
特許番号
US04602027

関連ノート

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