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Hydrochloric Acid → (2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 1590482
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1590482
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27][N:28]2[CH2:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])[CH2:10]1)(C(C)(C)C)(C)C.Cl>CO>[O:34]=[C:29]1[NH:30][C:31](=[O:33])[CH2:32][N:28]1[CH2:27][C@@H:11]1[CH2:10][C@@H:9]([OH:8])[CH2:13][N:12]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 15056134(2S,4R)-4-t-butyldimethylsilyloxy-2-(2,4-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 15056135(2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (2S,4R)-4-t-butyldimethylsilyloxy-2-(2,4-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.78 g) in a mixture of methanol (100 ml) and conc. hydrochloric acid (1.62 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was evaporated in vacuo. The resulting residue was dissolved in toluene (30 ml) and the solution was concentrated under reduced pressure to give a residue. The residue was chromatographed on silica gel (60 g) eluting with a mixture of dichloromethane and acetone (2:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3.27 g).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in toluene (30 ml)
  3. concentrationthe solution was concentrated under reduced pressure
  4. customto give a residue
  5. customThe residue was chromatographed on silica gel (60 g)
  6. washeluting with a mixture of dichloromethane and acetone (2:1 V/V)
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ecdf1f4572164947b679f36b630c0062
Quelldatensatz
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05202437

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