Pyridine → (S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

HRID 1620924

Reaktionsgleichung

Reaktionsgleichung von HRID 1620924
C(O[C:6]([NH:8][C@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.N1C=CC=CC=1.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>ClC(Cl)C.ClCCl>[O:7]=[C:6]1[NH:8][C@@H:9]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:21][O:22]1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 77773Toluene-p-sulphonic anhydrideHCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

Produkt 1

HCID 11241814(S)-Benzyl 2-(2-oxooxazolidin-4-YL)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To a solution of the alcohol (95.7 g) from Step 1 in dichloroethane (925 mL) was added pyridine (625 mL) and the mixture was cooled to 0-5° C. Anhydrous p-toluenesulfonic anhydride (105.7 g) was added and the mixture was warmed to room temperature and stirred for 1 hour and then heated to 90° C. for 2 hours. The mixture was cooled, diluted with dichloromethane (1000 mL) and washed with 1N HCl (3×600 mL). The organic layer was washed with brine, dried with sodium sulfate and the solvents were removed in vacuo. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes in a 1:1 ratio followed by ethyl acetate to yield benzyl [(4S)-2-oxo-1,3-oxazolidin-4-yl]acetate.

Aufarbeitung

  1. temperaturethe mixture was warmed to room temperature
  2. temperatureheated to 90° C. for 2 hours
  3. temperatureThe mixture was cooled
  4. washwashed with 1N HCl (3×600 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried with sodium sulfate
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-25a323c1ce15472a9ecd621f28137146
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772336B2

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