Tris(furan-2-yl)phosphane → N-{[(5S)-3-(4-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

HRID 747245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747245
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Sn](C)(C)C)=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3]1.Br[C:23]1[S:27][C:26]([C:28]2[CH2:32][CH:31]([CH2:33][OH:34])[O:30][N:29]=2)=[CH:25][CH:24]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[OH:34][CH2:33][CH:31]1[O:30][N:29]=[C:28]([C:26]2[S:27][C:23]([C:10]3[CH:11]=[CH:12][C:7]([N:6]4[CH2:5][C@H:4]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:3][C:2]4=[O:1])=[CH:8][CH:9]=3)=[CH:24][CH:25]=2)[CH2:32]1

Komponenten

5

Edukt 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 14987823N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamideHCID 17954475[3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Produkt 1

HCID 59749493N-{[(5S)-3-(4-{5-[5-(Hydroxymethyl)-4,5-dihydroisoxazol-3-yl]thien-2-yl}phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamideAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)Katalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

N-({(5S)-2-Oxo-3-[4-(trimethylstannyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide (500 mg, 1.26 mM), [3-(5-bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol (330 mg, 1.26 mM), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (130 mg, 0.126 mM) and tri-2-furylphosphine (58 mg, 0.252 mM) were placed in a flask. The solids were degassed and placed under nitrogen. Anhydrous dioxane (10 ml) was added and the suspension was heated at 90° C. for 16 hours. The reaction mixture was cooled and the solvent was evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give the title compound (220 mg).

Aufarbeitung

  1. customThe solids were degassed
  2. additionAnhydrous dioxane (10 ml) was added
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was chromatographed on silica gel eluting with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-024e81dc726548a48e69f0ca86a3a623
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396847B2

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