Water → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyidimethylsilyl)oxy-1-phenyl ethoxy}-azetidin-2-one

HRID 1075646ノート

反応式

HRID 1075646 の反応式
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]2[C@H:26](OC(=O)C)[NH:25][C:24]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:32]([O:39][CH2:40][CH:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[OH:42])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].O>C1C=CC=CC=1.C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]2[C@@H:26]([O:42][CH:41]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:40][O:39][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[NH:25][C:24]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 3

HCID 962WaterHCID 113911162-(Tert-butyldimethylsilyl)oxy-1-phenylethanolHCID 57304138(3S,4S)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-acetoxy-azetidin-2-one

生成物 1

HCID 70094998(3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyidimethylsilyl)oxy-1-phenyl ethoxy}-azetidin-2-one収率 7%

試薬・触媒・溶媒 3

HCID 2724192Zinc acetate (USP)触媒HCID 241Benzene溶媒HCID 1140Toluene溶媒

実験手順

A mixture of (3S,4S)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-acetoxy-azetidin-2-one (4.36 g, 10.30 mmole), 2-(tert-butyldimethylsilyl)oxy-1-phenylethanol (2.6 g, 10.30 mmole), and zinc acetate dihydrate (2.26 g, 10.30 mmole) in a mixture of benzene (70 ml) and toluene (70 ml) was refluxed overnight using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (4:3) as eluent and (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(tert-butyidimethylsilyl)oxy-1-phenyl ethoxy}-azetidin-2-one was obtained (440 mg, 7% yield).

後処理

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-879e4df60c444ac7927be2d8e549d8a1
出典データセット
uspto-grants-1999_05
特許番号
US05905076

反応ノート

読み込み中…