N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 178453838, compound

HRID 1197077Notes

Reaction equation

HRID 1197077 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15](ON1C(=O)CCC1=O)=[O:16]>CN(C=O)C>[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])=[O:16]

Participants

4

Reactant 2

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 178418600HCID 178418600, compound

Product 1

HCID 178453838HCID 178453838, compoundYield 151.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

After 109.2 g (0.27 mol) of H-Arg-CHA.2HCl was dissolved in 290 ml of DMF, 70.2 ml (0.54 mol) of NEM was added to the solution. Further 81.7 g (0.3 mol) of BOC-Gly-OSu was added thereto at 0° to 5° C. The resulting mixture was reacted at room temperature for 18 hours. After completion of the reaction, DMF was distilled under reduced pressure. The residue was dissolved in 500 ml of MeOH and the solution was reprecipitated in 8 liters of AcOEt. The precipitated crystals were taken by filtration and dried to give 135.8 g (100%) of BOC-Gly-Arg-CHA.HCl.

Workup

  1. addition70.2 ml (0.54 mol) of NEM was added to the solution
  2. customat 0° to 5° C
  3. customThe resulting mixture was reacted at room temperature for 18 hours
  4. distillationwas distilled under reduced pressure
  5. dissolutionThe residue was dissolved in 500 ml of MeOH
  6. customthe solution was reprecipitated in 8 liters of AcOEt
  7. filtrationThe precipitated crystals were taken by filtration
  8. customdried

Sources & evidence

ORD record
ord-bb4d0f574c3644f39a6558baec754ba8
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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