Phosgene → (S)-4-(4-Nitrobenzyl)oxazolidin-2-one

HRID 1608972Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608972
[NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH2:3][OH:4].[OH-].[K+].[C:17](Cl)(Cl)=[O:18]>C1(C)C=CC=CC=1.O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C@H:2]2[CH2:3][O:4][C:17](=[O:18])[NH:1]2)=[CH:7][CH:8]=1)([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 10397777(S)-2-Amino-3-(4-nitrophenyl)propan-1-ol

Produkt 1

HCID 10353477(S)-4-(4-Nitrobenzyl)oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product from step (b) (4.9 g) was suspended in toluene, the suspension cooled to 0° C. and a solution of potassium hydroxide (7.0 g) in water (56 ml) added dropwise. A solution of phosgene (62.5 ml of a 12% w/v solution in toluene) was added dropwise to the resulting solution over 30 minutes and stirring continued for 1 hour. The mixture was extracted with ethyl acetate and the extracts washed with brine, dried and evaporated in vacuo to give a yellow oil. Crystallisation from ethyl acetate gave the desired product as pale yellow crystals (2.3 g).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extracts washed with brine
  3. customdried
  4. customevaporated in vacuo
  5. customto give a yellow oil
  6. customCrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d9b211ccbf36478eb6738b4ed66f9abb
Quelldatensatz
uspto-grants-1995_03
Patentnummer
US05399574

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