Potassium Carbonate → (S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

HRID 25237

Reaktionsgleichung

Reaktionsgleichung von HRID 25237
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[N+](C1C=C(S(O[CH2:25][C@H:26]2[O:28][CH2:27]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:25][C@H:26]1[O:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 41154952-Amino-3-Nitrophenol

Produkt 1

HCID 15049327(S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropaneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

5 g (0.032 mol) of 2-amino-3-nitrophenol, 8 g (0.032 mol) of (S)-(+)-glycidyl 3-nitrobenzenesulfonate and 8.9 g of K2CO3 are mixed in 80 ml of acetone and the mixture is refluxed for 18 hours. Filtration is carried out, the solvent is evaporated under reduced pressure and the crude product is purified by flash chromatography, elution being carried out with a 7/3 cyclohexane/ethyl acetate mixture. The solid product obtained is triturated in ethyl ether and 5.67 g of the title product are obtained. M.p.: 107-109°. αD+28.1 (c=0.5%, MeOH).

Aufarbeitung

  1. temperaturethe mixture is refluxed for 18 hours
  2. filtrationFiltration
  3. customthe solvent is evaporated under reduced pressure
  4. customthe crude product is purified by flash chromatography, elution
  5. customThe solid product obtained
  6. customis triturated in ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f4b14f780c4148528ec5549cc4115d8e
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858629B1

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