HCID 124544363, compound → HCID 178451027, compound

HRID 1197079Notes

Reaction equation

HRID 1197079 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[NH:17]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@@H:18]([C:28](ON1C(=O)CCC1=O)=[O:29])[CH2:19][CH2:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C>[NH:17]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C@@H:18]([C:28]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4])=[O:29])[CH2:19][CH2:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 124544363HCID 124544363, compoundHCID 178512899HCID 178512899, compound

Product 1

HCID 178451027HCID 178451027, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 4.4 g (10 mM) of H-Gly-Arg-CHA.2HCl was dissolved in 20 ml of 0.75N NEM/DMF, 4.3 g (10 mM) of Z-D-Glu(OtBu)-OSu was added to the solution while cooling to 0° to 5° C. with stirring. The resulting mixture was reacted at room temperature for 15 hours. After completion of the reaction, the solvent was distilled under reduced pressure. The residue was dissolved in MeOH and the solution was reprecipitated in 1 liter of AcOEt. The precipitated crystals were taken by filtration and dried to give 6.1 g (84.5%) of Z-D-Glu(OtBu)-Gly-Arg-CHA.HCl.

Workup

  1. additionwas added to the solution
  2. temperaturewhile cooling to 0° to 5° C.
  3. customThe resulting mixture was reacted at room temperature for 15 hours
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled under reduced pressure
  6. dissolutionThe residue was dissolved in MeOH
  7. customthe solution was reprecipitated in 1 liter of AcOEt
  8. filtrationThe precipitated crystals were taken by filtration
  9. customdried

Sources & evidence

ORD record
ord-8d66c6094149480283f30602dcf96c6a
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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