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

HRID 400235

반응식

HRID 400235 반응식
[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

참가 물질

8

반응물 4

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

생성물 2

HCID 13097Triphenylphosphine OxideHCID 68157Oxazoline

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d86487837e574210b2cf97c5816a36ea
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827868

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