Hexanoic Acid → (5R)-3-(4-hexanoyloxyphenyl)-5-phenyl-2-oxazolidinone

HRID 54873

Reaktionsgleichung

Reaktionsgleichung von HRID 54873
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[C:20](O)(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10][C:9]2=[O:19])=[CH:6][CH:7]=1)(=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

6

Edukt 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 54314065(5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone

Produkt 1

HCID 54082322(5R)-3-(4-hexanoyloxyphenyl)-5-phenyl-2-oxazolidinoneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.50 g (1.96 mM) of (5R)-3-(4-hydroxyphenyl)-5-phenyl-2-oxazolidinone synthesized in Example 2, 0.26 g of hexanoic acid and 20 ml of methylene chloride were placed in 50 ml-round bottomed flask, followed by stirring to form a solution. To the solution, 0.43 g (2.08 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-dimethylaminopyridine were added in succession, followed by stirring for 8 hours at room temperature. The precipitated N,N'-dicyclohexylurea was filtered out and the filtrate was evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1) and recrystallized from methanol to obtain 0.36 g of (5R)-3-(4-hexanoyloxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 52.0%).

Aufarbeitung

  1. customto form a solution
  2. stirringby stirring for 8 hours at room temperature
  3. filtrationThe precipitated N,N'-dicyclohexylurea was filtered out
  4. customthe filtrate was evaporated under reduced pressure
  5. customto obtain a residue
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=20/1)
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-263075cfa31f47fbaf9c7cbb4f81464f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624600

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