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2-Mercaptoethanol → (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyrrolidine

HRID 1650829
Notes
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Reaction equation

HRID 1650829 reaction equation
[N+:1]([C:4]1[CH:58]=[CH:57][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:14][C@H:13]2[CH2:37][N:38]2[CH2:43][CH2:42][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([N+:54]([O-:56])=[O:55])=[CH:50][CH:49]=3)=[O:45])[CH2:40][CH2:39]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].SCCO>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[SH:17][C@@H:15]1[CH2:16][N:12]([C:10]([O:9][CH2:8][C:7]2[CH:57]=[CH:58][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[C@H:13]([CH2:37][N:38]2[CH2:39][CH2:40][N:41]([C:44]([O:46][CH2:47][C:48]3[CH:49]=[CH:50][C:51]([N+:54]([O-:56])=[O:55])=[CH:52][CH:53]=3)=[O:45])[CH2:42][CH2:43]2)[CH2:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 15672-MercaptoethanolHCID 15056128(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methyl-4-(triphenylmethylthio)pyrrolidine

Product 1

HCID 15056064(2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)-piperazin-1-yl]methylpyrrolidineYield 48.3%

Reagents, catalysts & solvents 3

HCID 1140Toluene
Solvent
HCID 6422Trifluoroacetic acidSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-1- (4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methyl-4-(triphenylmethylthio)pyrrolidine (2.76 g) in trifluoroacetic acid (15 ml) was added 2-mercaptoethanol (0.31 ml) under ice-cooling and the mixture was stirred at ambient temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in toluene (20 ml) and the solution was evaporated in vacuo to give a syrup. The syrup was dissolved in ethyl acetate (60 ml) and washed successively with saturated aqueous sodium hydrogen carbonate (30 ml) and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure 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)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl]methylpyrrolidine (0.93 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give a residue
  4. customthe solution was evaporated in vacuo
  5. customto give a syrup
  6. washwashed successively with saturated aqueous sodium hydrogen carbonate (30 ml) and saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  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-673dbd217f094e4caa7bfb1a4d7ceb3c
Source dataset
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04925838

Reaction notes

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