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

HRID 1650830Notes

Reaction equation

HRID 1650830 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C@@H:10]1[CH2:14][C@H:13]([S:15]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:12][N:11]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:36])(=[O:3])[NH2:2].SCCO>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[C:1]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C@@H:10]1[CH2:14][C@H:13]([SH:15])[CH2:12][N:11]1[C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=1)=[O:36])(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 15672-MercaptoethanolHCID 15056121(2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

Product 1

HCID 57065684(2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 52.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (1.76 g) in trifluoroacetic acid (10 ml) was added 2-mercaptoethanol (0.38 ml) under ice-cooling and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure to give a residue The residue was dissolved in toluene (10 ml) and the solution was evaporated in vacuo. The resulting residue was dissolved in ethyl acetate (50 ml), washed successively with saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.58 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a residue The residue
  4. customthe solution was evaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in ethyl acetate (50 ml)
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a residue
  10. customThe residue was chromatographed on silica gel (100 g)
  11. washeluting with a mixture of dichloromethane and acetone (9:1 V/V)
  12. additionThe fractions containing the desired compound
  13. customwere collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-52a4751599884f05875ebf434d5db5ac
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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