Morpholine → benzyl 2(S)-morpholinocarbonyloxy-3-phenylpropionate

HRID 847561ノート

反応式

HRID 847561 の反応式
[OH:1][C@@H:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl[C:21](OC(Cl)(Cl)Cl)=[O:22].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O1CCCC1>[O:31]1[CH2:32][CH2:33][N:28]([C:21]([O:1][C@@H:2]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[O:22])[CH2:29][CH2:30]1

参加物

5

反応物 3

HCID 8083MorpholineHCID 10426DiphosgeneHCID 10377698Benzyl (S)-(-)-2-hydroxy-3-phenylpropionate

生成物 1

HCID 18638974benzyl 2(S)-morpholinocarbonyloxy-3-phenylpropionate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of benzyl 2(S)-hydroxy-3-phenylpropionate (256 mg) in dry tetrahydrofuran (10 ml) was added trichloromethyl chloroformate (0.122 ml). The mixture was refluxed for 18 hours. The mixture was cooled to 0° C., and morpholine (348 mg) was added thereto. The mixture was stirred at the same temperature for 3 hours. After evaporation of the solvent, the residue was dissolved in ethyl acetate (40 ml). The solution was washed with 5% hydrochloric acid, 1 M sodium bicarbonate solution and water successively, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (25% ethyl acetate in n-hexane as eluent) to give benzyl 2(S)-morpholinocarbonyloxy-3-phenylpropionate (367 mg) as an oil.

後処理

  1. temperatureThe mixture was refluxed for 18 hours
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in ethyl acetate (40 ml)
  4. washThe solution was washed with 5% hydrochloric acid, 1 M sodium bicarbonate solution and water successively
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (25% ethyl acetate in n-hexane as eluent)

出典と根拠

ORDレコード
ord-cc1497f6a51e4b9698fc104a1977f7d5
出典データセット
uspto-grants-1992_08
特許番号
US05142048

反応ノート

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