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

HRID 847561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847561
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cc1497f6a51e4b9698fc104a1977f7d5
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05142048

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