Potassium Carbonate → (s)-Methyl 2-oxooxazolidine-4-carboxylate

HRID 54836

Reaktionsgleichung

Reaktionsgleichung von HRID 54836
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[C:10]([O-])([O-])=[O:11].[K+].[K+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O.C1(C)C=CC=CC=1>[C:4]([C@@H:5]1[CH2:7][O:8][C:10](=[O:11])[NH:6]1)([O:3][CH3:2])=[O:9]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 94429TriphosgeneHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 385463(s)-Methyl 2-oxooxazolidine-4-carboxylateAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To (S)-serine methyl ester hydrochloride (20 g, 128.64 mmol) in water (230 ml) was added KHCO3 (14.16 g, 141.52 mmol) and K2CO3 (19.56 g, 141.52 mmol) at room temperature. It was then cooled by an ice bath and triphosgene (19.04 gm, 64.32 mmol) was added in toluene (192 ml) via an addition funnel over 25 minutes. The reaction mixture turned cloudy. After 2 h, reaction phases were separated and the aqueous layer was lyophilized to yield (S)-4-carbomethoxy-2-oxazolidinone as a white solid (16.5 g) in 88% yield.

Aufarbeitung

  1. temperatureIt was then cooled by an ice bath
  2. customreaction phases
  3. customwere separated

Quellen und Nachweise

ORD-Eintrag
ord-5e16446cfae24e40a58886efbd0df072
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623087

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