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

HRID 1650848노트

반응식

HRID 1650848 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8857Ethyl Acetate용매

실험 절차

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:l,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).

후처리

  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:l,V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-60ae3a55d30f4fa8b390ecaa18eccd2b
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925838

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