2-Mercaptoethanol → HCID 57213191, compound

HRID 1650831Notes

Reaction equation

HRID 1650831 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]2[CH2:13][C@H:12]([S:14]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:11][N:10]2[C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[O:35])[CH2:4][CH2:3]1.SCCO>FC(F)(F)C(O)=O.C(OCC)(=O)C>[SH:14][C@@H:12]1[CH2:11][N:10]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[O:35])[C@H:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH2:13]1

Participants

5

Reactant 2

HCID 15672-MercaptoethanolHCID 15056131HCID 15056131, compound

Product 1

HCID 57213191HCID 57213191, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-2-(4-methylpiperazin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (6.85 g) in trifluoroacetic acid (35 ml) was added 2-mercaptoethanol (1.13 ml) under ice-cooling and the mixture was stirred at ambient temperature for 15 minutes. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in toluene (40 ml) and the solution was evaporated in vacuo to give a syrup. The syrup was dissolved in ethyl acetate (100 ml) and washed successively with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, dried over 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 (10:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-mercapto-2-(4-methylpiperazin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.14 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in toluene (40 ml)
  4. customthe solution was evaporated in vacuo
  5. customto give a syrup
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  7. dry with materialdried over 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 (10:1 V/V)
  12. additionThe fractions containing the desired compound
  13. customwere collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-0122af4634f348f4952f581db459958c
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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