Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isothiazol-3-yloxymethyl)oxazolidin-2-one

HRID 1167422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167422
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH2:30][CH2:31][O:32][CH2:33][CH:34]=3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1.O[C:37]1[CH:41]=[CH:40][S:39][N:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[S:39]1[CH:40]=[CH:41][C:37]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH2:30][CH2:31][O:32][CH2:33][CH:34]=4)=[C:25]([F:35])[CH:24]=3)[CH2:18]2)=[N:38]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 186848415(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-oneHCID 178516663HCID 178516663, Verbindung

Produkt 1

HCID 497387(5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-(isothiazol-3-yloxymethyl)oxazolidin-2-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropylazodicarboxylate (227 mg, 1.12 mmol) was added dropwise, at ambient temperature, to a stirred solution of 5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (300 mg, 1.02 mmol ; see Example 1), 3-hydroxyisothiazole (114 mg, 1.13 mmol) and triphenylphosphine (304 mg, 1.16 mmol) in THF (8.0 ml). The resulting solution was stirred at room temperature for 30 minutes before evaporating the solvent to give an orange oil. It was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (3:2)) to give the title product (257 mg, 67%) as a colourless crystalline solid. MS: ESP+ (M+H)+=377.

Aufarbeitung

  1. custombefore evaporating the solvent
  2. customto give an orange oil
  3. customIt was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (3:2))

Quellen und Nachweise

ORD-Eintrag
ord-f9d5f05f4d4d4fe7b204bb5aa1b4530e
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617339B1

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