N,N,N',N'-Tetramethylazodicarboxamide → Triphenylphosphine Oxide

HRID 400235

Reaktionsgleichung

Reaktionsgleichung von HRID 400235
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:21]([C:23](N=NC(N(C)C)=O)=[O:24])C.C(N(CC)C(C)C)(C)C.C(Cl)(Cl)(Cl)Cl>C(#N)C.C(OCC)(=O)C>[O:24]1[CH2:14][CH2:19][N:21]=[CH:23]1.[C:14]1([P:7](=[O:24])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 81531Diisopropylethylamine

Produkt 2

HCID 13097Triphenylphosphine OxideHCID 68157Oxazoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triphenylphosphine (654 mg, 2.46 mmol) was added to a stirred solution of diamide F (400 mg, 0.75 mmol) in acetonitrile (15 mL). After a few minutes, N,N-diisopropylethyl amine (440 μl, 2.52 mmol) was added. Addition of carbon tetrachloride (800 μl) followed. The mixture was stirred for 24 hours, diluted with ethyl acetate (100 mL) and washed with aqueous sodium bicarbonate solution and brine. The organic extract was dried (magnesium sulfate), filtered and concentrated. The residue was chromatographed on a silica gel column and eluted with 50% ethyl acetate in hexanes, followed by ethyl acetate and 2-5% methanol in ethyl acetate to obtain oxazoline G (450 mg, contaminated with triphenylphosphine oxide) as a mixture of diastereomers.

Aufarbeitung

  1. waitAfter a few minutes
  2. washwashed with aqueous sodium bicarbonate solution and brine
  3. extractionThe organic extract
  4. dry with materialwas dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column
  8. washeluted with 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d86487837e574210b2cf97c5816a36ea
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827868

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