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

HRID 57373

Reaktionsgleichung

Reaktionsgleichung von HRID 57373
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>ClCCCl.C(Cl)Cl>[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)acetateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate (16.3 g, 52.7 mmol) and pyridine (10.65 ml, 132 mmol) in DCE (157 mL) at 0° C. was added p-toluenesulfonic anhydride (17.10 g, 52.4 mmol) in two portions over 5 min. The mixture was stirred for a few minutes, then allowed to warm to room temperature and stirred for 1 hr. The mixture was heated for 6 hr at 92° C. and then allowed to cool to room temperature. The mixture was diluted with DCM (80 mL), washed with 1N aqueous HCl solution (2×200 mL), brine (200 mL), and saturated aqueous sodium bicarbonate solution (100 mL). The organic layer was dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 220 g, EtOAc/heptane=5/95 to 75/25] to provide (S)-benzyl 2-(2-oxooxazolidin-4-yl)acetate (10.0 g) as a white solid. MS m/z 236.2 (M+H)+; Rt-0.59 min.

Aufarbeitung

  1. stirringstirred for 1 hr
  2. temperatureThe mixture was heated for 6 hr at 92° C.
  3. temperatureto cool to room temperature
  4. washwashed with 1N aqueous HCl solution (2×200 mL), brine (200 mL), and saturated aqueous sodium bicarbonate solution (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography [SiO2, 220 g, EtOAc/heptane=5/95 to 75/25]

Quellen und Nachweise

ORD-Eintrag
ord-04ae88f90f014ad4b76a2e05c1e7a0e4
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

Verknüpfte Notizen

Wird geladen…