Dicyclohexylcarbodiimide → HCID 86745504, compound

HRID 1534970Notes

Reaction equation

HRID 1534970 reaction equation
[C:1]([S:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:28]1(=[O:33])[N:27]([N:13]([C:11](=[O:12])[CH2:10][S:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])=[O:16])[C:31](=[O:32])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 185457Betiatide

Product 1

HCID 86745504HCID 86745504, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 ml round bottom flask, 0.37 g (1 mmole) of benzoylmercaptoacetylglycylglycylglycine and 0.126 g (1.1 mmole) of N-hydroxy succinimide are dissolved in approximately 25 mL of tetrahydrofuran and cooled to 5°-10° C. in an ice bath. To this solution, 0.23 g (1.1 mmole) of N,N'-dicyclohexylcarbodiimide is added. The solution is allowed to warm to room temperature and is stirred for 48 hours and the course of the reaction followed by TLC. The precipitate is removed by filtering; the filtered solution is evaporated to dryness under vacuum. The residue is redissolved in 50-60 mL of dichloromethane; this solution is filtered and evaporated to dryness under vacuum. The residue is redissolved in 5-6 mL ethanol with warming and allowed to crystallize for 3-4 hours. The crystals of product succinimidyl-MAGGG are recovered by filtration.

Workup

  1. temperaturecooled to 5°-10° C. in an ice bath
  2. customThe precipitate is removed
  3. filtrationby filtering
  4. customthe filtered solution is evaporated to dryness under vacuum
  5. dissolutionThe residue is redissolved in 50-60 mL of dichloromethane
  6. filtrationthis solution is filtered
  7. customevaporated to dryness under vacuum
  8. dissolutionThe residue is redissolved in 5-6 mL ethanol
  9. temperaturewith warming
  10. customto crystallize for 3-4 hours
  11. filtrationThe crystals of product succinimidyl-MAGGG are recovered by filtration

Sources & evidence

ORD record
ord-7da83613101d4486ba67887d88dc4eb3
Source dataset
uspto-grants-1992_02
Patent number
US05091514

Reaction notes

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