Cyanogen Bromide → HCID 131727697, compound

HRID 1157362Notes

Reaction equation

HRID 1157362 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:17]2[CH:22]=[C:21]([I:23])[C:20]([O-:24])=[C:19]([I:25])[CH:18]=2)=[C:8]2[CH:14]=[C:13]([I:15])[C:11](=[O:12])[C:10]([I:16])=[CH:9]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+].[CH2:31]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:42](=[O:53])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([NH2:52])[CH:47]=2)[NH2:44])[CH2:38][CH2:37]1)=[O:35])[CH3:32].C([O-])(=O)C.[Na+].[N:59]#[C:60]Br>C(O)C>[CH:1]1[CH:6]=[C:5]([C:7]([C:8]2[CH:9]=[C:10]([I:16])[C:11]([O-:12])=[C:13]([I:15])[CH:14]=2)=[C:17]2[CH:18]=[C:19]([I:25])[C:20](=[O:24])[C:21]([I:23])=[CH:22]2)[C:4]([C:26]([O-:28])=[O:27])=[CH:3][CH:2]=1.[Na+:29].[Na+:29].[CH2:31]([O:33][C:34]([N:36]1[CH2:37][CH2:38][N:39]([C:42](=[O:53])[C@H:43]([CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[C:48]([NH:52][C:60]#[N:59])[CH:47]=2)[NH2:44])[CH2:40][CH2:41]1)=[O:35])[CH3:32]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 131727699HCID 131727699, compound

Product 1

HCID 131727697HCID 131727697, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

TIPPS-3-amino-(L)-phenylalanine-4-ethoxycarbonylpiperazide (14.6 g; 24.9 mmol), sodium acetate (anhydrous) (5.11 g; 62.2 mmol) and cyanogen bromide (2.9 g; 27.4 mmol) were dissolved in ethanol and the solution was stirred at RT for 10 h. After evaporating the solvent, the residue was taken up in ethyl acetate and the solution was extracted with 5% KHSO4, 5% NaHCO3 and distilled water. After evaporating the solvent, the crude product was purified chromatographically over silica gel.

Workup

  1. customAfter evaporating the solvent
  2. extractionthe solution was extracted with 5% KHSO4, 5% NaHCO3
  3. distillationdistilled water
  4. customAfter evaporating the solvent
  5. customthe crude product was purified chromatographically over silica gel

Sources & evidence

ORD record
ord-ec965f91887d4b54bc0414ed790aa997
Source dataset
uspto-grants-2010_10
Patent number
US07807681B2

Reaction notes

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