Trifluoroacetic acid → 3-(trans-1-benzyl-4-ethyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

HRID 1378464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378464
[C:1]([N:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][O:9][C:8]1=[O:18])(=[O:6])/[CH:2]=[CH:3]/[CH2:4][CH3:5].[CH2:19]([N:26]([CH2:30][Si](C)(C)C)[CH2:27]OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:19]([N:26]1[CH2:30][C@@H:3]([CH2:4][CH3:5])[C@H:2]([C:1]([N:7]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][O:9][C:8]2=[O:18])=[O:6])[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11096863(S,E)-3-(pent-2-enoyl)-4-phenyloxazolidin-2-one

Produkt 1

HCID 228718283-(trans-1-benzyl-4-ethyl-3-pyrrolidinylcarbonyl)-4-(S)-phenyl-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound from step 7b (490 mg, 2 mmol) was dissolved in methylene chloride (9 mL), and the solution was cooled to 0° C. and flushed with N2. N-benzyl-N-(methoxymethyl)trimethylsilylmethyl-amine (498 mg, 2.1 mmol) was added, the mixture was stirred for 20 minutes and trifluoroacetic acid (1M, 0.2 mL, 0.20 mmol) was added dropwise over 20 minutes with stirring at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 24 hours, then diluted with 50 mL of methylene chloride, washed with 10% aqueous K2CO3 and dried over Na2SO4. The solvent was removed and the residue was dried under vacuum (767 mg). The isomers were separated by medium pressure liquid chromatography on silica gel, eluting with 0.5% methanol/methylene chloride. The major isomer (3R,4R) (290 mg) was taken to the next step. MS m/z 379 (M+H)+.

Aufarbeitung

  1. customflushed with N2
  2. stirringwith stirring at 0° C
  3. stirringThe mixture was stirred at 0° C. for 1 hour and at room temperature for 24 hours
  4. washwashed with 10% aqueous K2CO3
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe residue was dried under vacuum (767 mg)
  8. customThe isomers were separated by medium pressure liquid chromatography on silica gel
  9. washeluting with 0.5% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-10eff7f29a784b55ac02e982eaf7e4b4
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668164

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