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Triethylamine → (3S,4S)-3-{N-(trans-2-phenyl-eth-1-enesulfonyl)-beta-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one

HRID 619707
ノート
印刷プレビュー

反応式

HRID 619707 の反応式
C(OC([NH:11][C@H:12]([C:24]([C@@H:26]1[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[N:28]([NH2:34])[C:27]1=[O:35])=[O:25])[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)=O)C1C=CC=CC=1.[H][H].C(N(CC)CC)C.[C:45]1(/[CH:51]=[CH:52]/[S:53](Cl)(=[O:55])=[O:54])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>[Pd].C(OCC)(=O)C.C1COCC1>[C:45]1(/[CH:51]=[CH:52]/[S:53]([NH:11][C@H:12]([C:24]([C@@H:26]2[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[N:28]([NH2:34])[C:27]2=[O:35])=[O:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:55])=[O:54])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 5369377(E)-2-phenylethene-1-sulfonyl chlorideHCID 86754557(3S,4S)-3-{N-benzyloxycarbonyl-beta-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86754560(3S,4S)-3-{N-(trans-2-phenyl-eth-1-enesulfonyl)-beta-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one収率 12%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
-15 °C

実験手順

(3S,4S)-3-{N-benzyloxycarbonyl-β-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one (237 mg, 0.5 mmol) obtained in example 8, was hydrogenated with 400 mg of 10% palladium on activated carbon in ethyl acetate (20 ml) and THF (10 ml) at 50 psi hydrogen pressure at room temperature for 2 hrs. After removal of catalyst by filtration, the desubstituted (3S,4S)-3{β-(2-naphthyl)-L-alanyl}-amino-4-acetoxy-azetidin-2-one was cooled to -15° C. Then triethylamine (50 mg, 0.5 mmol) and trans-2-phenyl-eth-1-ene sulfonyl chloride (101 mg, 0.5 mmol) were added at -15° C. Stirring was continued at a bath temperature of -10 to 0° C. for 1 hr and 5° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with cold saturated NaHCO3 solution, water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:1) as eluent and the title compound (30 mg) was obtained.

後処理

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. customwas continued at a bath
  4. custom5° C. overnight
  5. washwashed with cold saturated NaHCO3 solution, water, brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of solvent
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-feee0f67a1fb42a48a24a626490a242f
出典データセット
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05959123

反応ノート

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