Dicyclohexylcarbodiimide → Carbonyl-4-benzoylthiopyrrolidine

HRID 744885Notes

Reaction equation

HRID 744885 reaction equation
[N+](C1C=CC(COC(NCCOCC(O)=O)=O)=CC=1)([O-])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[N+](C1C=CC(COC([N:58]2[CH2:62][C@@H:61]([S:63][C:64](=[O:71])[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[CH2:60][C@H:59]2[C:72](N2CCNCC2)=[O:73])=O)=CC=1)([O-])=O>O1CCCC1.C(N(CC)CC)C>[C:72](=[C:59]1[CH2:60][CH:61]([S:63][C:64](=[O:71])[C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[CH2:62][NH:58]1)=[O:73]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 194224242-(2-(p-Nitrobenzyloxycarbonylamino)ethoxy)acetic acidHCID 57220211(2s,4s)-1-(p-Nitrobenzyloxycarbonyl)-2-(piperazine-1-yl)carbonyl-4-benzoylthiopyrrolidine

Product 1

HCID 131719586Carbonyl-4-benzoylthiopyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 209 mg of 2-(2-(p-nitrobenzyloxycarbonylamino)ethoxy)acetic acid, followed by stirring on an ice bath. To this were added 161 mg of 1-hydroxybenzotriazole and 433 mg of dicyclohexylcarbodiimide, followed, after 1 hour of stirring at the same temperature, by the addition of 523 mg of (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-(piperazine-1-yl)carbonyl-4-benzoylthiopyrrolidine and 0.146 m of triethylamine and subsequent 1 hour of stirring. After removing insoluble material by filtration, the resulting filtrate was evaporated under a reduced pressure, and a residue was subjected to a silica gel column chromatography to yield 402 mg of (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-(4-(2-(2) -(p-nitrobenzyloxycarbonylamino) ethoxy)acetyl)piperazine-1-yl)carbonyl-4-benzoylthiopyrrolidine as the compound of interest.

Workup

  1. stirringof stirring
  2. customAfter removing insoluble material
  3. filtrationby filtration
  4. customthe resulting filtrate was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-4ddc074a913f4d9db68b096f56a93c5a
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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