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

HRID 400235

反応式

HRID 400235 の反応式
[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

参加物

8

反応物 4

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

生成物 2

HCID 13097Triphenylphosphine OxideHCID 68157Oxazoline

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d86487837e574210b2cf97c5816a36ea
出典データセット
uspto-grants-1998_10
特許番号
US05827868

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