Tributylphosphine → 3-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl-oxymethyl)oxazolidin-2-one

HRID 1167431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167431
[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][OH:25])[O:21][C:20]3=[O:26])=[CH:15][C:14]=2[F:27])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:29]1[CH:33]=[CH:32][O:31][N:30]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Si:1]([O:8][CH:9]1[CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][O:25][C:29]4[CH:33]=[CH:32][O:31][N:30]=4)[O:21][C:20]3=[O:26])=[CH:15][C:14]=2[F:27])[CH2:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 213565963-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-oneHCID 178516613HCID 178516613, Verbindung

Produkt 1

HCID 699815973-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl-oxymethyl)oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(4-(3-t-Butyldimethylsilyloxy-1-azetidinyl)-3-fluorophenyl)-5(R)-hydroxymethyloxazolidin-2-one (WO 96/13502; 2.47 g, 6.25 mmol), 3-hydroxyisoxazole (580 mg, 6.86 mmol), and tributylphosphine (1.58 g, 7.8 mmol) were dissolved by stirring in dry tetrahydrofuran (100 ml) under nitrogen. The mixture was cooled in an ice-bath, and 1,1′-(azodicarbonyl)dipiperidine (1.96 g, 7.8 mmol) added dropwise over 10 minutes. The solution was stirred 18 hours, allowing the temperature to rise to ambient. Reduced azo compound was filtered off, and the solution evaporated to dryness and the residue triturated with ether. The residue was purified by chromatography on a silica flash column, eluting with a gradient from 50 to 75% EtOAc in isohexane. Relevant fractions were combined and evaporated to the product as an oil (1.31 g).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice-bath
  2. filtrationReduced azo compound was filtered off
  3. customthe solution evaporated to dryness
  4. customthe residue triturated with ether
  5. customThe residue was purified by chromatography on a silica flash column
  6. washeluting with a gradient from 50 to 75% EtOAc in isohexane
  7. customevaporated to the product as an oil (1.31 g)

Quellen und Nachweise

ORD-Eintrag
ord-f888938a6a9e4456a370a053d7a26fed
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617339B1

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