Methanol → HCID 15056144、化合物

HRID 1650841ノート

反応式

HRID 1650841 の反応式
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C:24]([N:26]2[CH2:30][CH2:29][N:28]([CH3:31])[C:27]2=[O:32])=O)[CH2:7]1)(=[O:4])=[O:3].CO>O1CCCC1.C(OCC)(=O)C>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([CH2:24][N:26]2[CH2:30][CH2:29][N:28]([CH3:31])[C:27]2=[O:32])[CH2:7]1)(=[O:4])=[O:3]

参加物

5

反応物 2

HCID 887MethanolHCID 18639280(2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)carbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

生成物 1

HCID 15056144HCID 15056144、化合物収率 48.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)carbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.70 g) in tetrahydrofuran (3.5 ml) was added 1.0M solution of borane-tetrahydrofuran complex in tetrahydrofuran (20.9 ml) and the mixture was stirred at ambient temperature for 1 hour and at 35°-40° C. for 2.5 hours. Methanol (20 ml) was added dropwise to the reaction mixture on ice-bath and the mixture was evaporated in vacuo. The resulting residue was dissolved in a mixture of methanol (20 ml) and 1.7M solution of hydrogen chloride in methanol (1 ml) and the mixture was allowed to stand overnight. The reaction mixture was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (60 ml) and the solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (30 g) eluting with a mixture of chloroform and methanol (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.33 g).

後処理

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in a mixture of methanol (20 ml) and 1.7M solution of hydrogen chloride in methanol (1 ml)
  3. waitto stand overnight
  4. customThe reaction mixture was evaporated in vacuo
  5. customto give a residue
  6. washthe solution was washed with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customThe resulting residue was chromatographed on silica gel (30 g)
  10. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

出典と根拠

ORDレコード
ord-f37202e5e54d4e54a4b257a3ac953343
出典データセット
uspto-grants-1990_05
特許番号
US04925838

反応ノート

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