O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 66914936, compound

HRID 491407Notes

Reaction equation

HRID 491407 reaction equation
N(C(OCC1C=CC=CC=1)=O)[C@H](C(N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1)=O)CC1C2C(=CC=CC=2)NC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:62][C@H:63]([C:71](O)=O)[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.[NH2:74][N:75]1[CH2:81][C:79](=[O:80])[NH:78][C:76]1=[O:77]>CN(C)C=O>[NH2:62][CH:63]([CH2:64][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)[CH:71]=[N:74][N:75]1[CH2:81][C:79](=[O:80])[NH:78][C:76]1=[O:77]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 14160293HCID 14160293, compoundHCID 131727440HCID 131727440, compound

Product 1

HCID 66914936HCID 66914936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Z-Trp-Trp-OH (0.1 mmol), 1-Hydroxybenzotriazolhydrate (0.1 mmol), and TBTU (0.1 mmol) were dissolved in dry dimethylformamide and stirred at r.t. After a few minutes Phe-Aminohydantoin (0.11 mmol) solved in dimethylformamide was added in portions and the reaction was allowed to reach room temperature over 18 hours. The solvent was removed and the residue was redissolved in ethyl acetate. The solution was washed with 1 mol/l HCl, and with 10% Na2CO3 and then dried over MgSO4. The reaction was filtered and the solvent was removed in vaccuo. The compound was purified by preparative HPLC.

Workup

  1. additionwas added in portions
  2. customThe solvent was removed
  3. dissolutionthe residue was redissolved in ethyl acetate
  4. washThe solution was washed with 1 mol/l HCl
  5. dry with materialwith 10% Na2CO3 and then dried over MgSO4
  6. filtrationThe reaction was filtered
  7. customthe solvent was removed in vaccuo
  8. customThe compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-01851933f9b744729797974d0a1ff119
Source dataset
uspto-grants-2009_05
Patent number
US07531517B2

Reaction notes

Loading…