Dicyclohexylcarbodiimide → HCID 57093356, compound

HRID 744882Notes

Reaction equation

HRID 744882 reaction equation
[C:1]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28]([OH:30])=O)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[N+:56]([C:59]1[CH:81]=[CH:80][C:62]([CH2:63][O:64][C:65]([NH:67][CH2:68][CH2:69][C@H:70]([OH:79])[C:71]([N:73]2[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]2)=[O:72])=[O:66])=[CH:61][CH:60]=1)([O-:58])=[O:57]>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]([S:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([C:28]([N:76]2[CH2:75][CH2:74][N:73]([C:71](=[O:72])[C@@H:70]([OH:79])[CH2:69][CH2:68][NH:67][C:65]([O:64][CH2:63][C:62]3[CH:80]=[CH:81][C:59]([N+:56]([O-:58])=[O:57])=[CH:60][CH:61]=3)=[O:66])[CH2:78][CH2:77]2)=[O:30])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 57165102HCID 57165102, compoundHCID 69943705HCID 69943705, compound

Product 1

HCID 57093356HCID 57093356, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1.04 g portion of (2S,4S)-4-benzoylthio-1-(p-nitrobenzyloxycarbonyl)proline was dissolved in 20 ml of tetrahydrofuran, and, with cooling on an ice bath, 0.55 g of N-hydroxybenzotriazole and 1.49 g of dicyclohexylcarbodiimide were added to the solution, followed by 1 hour of reaction with stirring at room temperature. To the solution were added 0.88 g of 1-((2S)-4-(p-nitrobenzyloxycarbonyl)amino-2-hydroxybutyryl)piperazine and 0.49 g of triethylamine, followed by 1 hour of reaction at room temperature. After concentration of the solvent, the residue was mixed with ethyl acetate to remove insoluble material, washed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order and then dried over sodium sulfate, followed by evaporation of the solvent under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography to yield 1.80 g of (2S,4S)-4-benzoylthio-1-(p-nitrobenzyloxycarbonyl) -2-((1-((2S)-4-(p-nitrobenzyloxycarbonyl) amino-2-hydroxybutyryl)piperazine-4-yl)carbonyl)pyrrolidine.

Workup

  1. temperaturewith cooling on an ice bath
  2. customfollowed by 1 hour of reaction
  3. customfollowed by 1 hour of reaction at room temperature
  4. customto remove insoluble material
  5. washwashed with sodium bicarbonate aqueous solution, citric acid aqueous solution and sodium chloride aqueous solution in that order
  6. dry with materialdried over sodium sulfate
  7. customfollowed by evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-a8a0068f27a24fd6a793b6c31e51dbe2
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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