2-Mercaptoethanol → (2S,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1590495ノート

反応式

HRID 1590495 の反応式
[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C@@H:9]1[CH2:13][C@H:12]([S:14]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11][N:10]1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:35].SCCO>FC(F)(F)C(O)=O.C(OCC)(=O)C>[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C@@H:9]1[CH2:13][C@H:12]([SH:14])[CH2:11][N:10]1[C:34]([O:36][CH2:37][C:38]1[CH:39]=[CH:40][C:41]([N+:44]([O-:46])=[O:45])=[CH:42][CH:43]=1)=[O:35]

参加物

5

反応物 2

HCID 15672-MercaptoethanolHCID 15056147(2S,4S)-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

生成物 1

HCID 15056150(2S,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine収率 49.7%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (2S,4S)-2-[(2S)-2-(hydroxymethyl)-pyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (5.74 g) in trifluoroacetic acid (30 ml) was added 2-mercaptoethanol (0.95 ml) under ice-cooling and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was evaporated in vacuo. The resulting residue was dissolved in toluene (30 ml) and the solution was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (100 ml) and the solution was washed in turn with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 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,4S)-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.77 g).

後処理

  1. temperaturecooling
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionThe resulting residue was dissolved in toluene (30 ml)
  4. customthe solution was evaporated in vacuo
  5. customto give a residue
  6. washthe solution was washed in turn with saturated aqueous sodium hydrogen carbonate and aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe resulting residue was chromatographed on silica gel (100 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-e57f99bb86f640d8befbeaf4768efa74
出典データセット
uspto-grants-1993_04
特許番号
US05202437

反応ノート

読み込み中…