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

HRID 1650833Notes

Reaction equation

HRID 1650833 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 15056135(2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 concentrated 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).

Workup

  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

Sources & evidence

ORD record
ord-7787283970374ae884785acb0baae14f
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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