Triethylamine → HCID 178454282, compound

HRID 1760485Notes

Reaction equation

HRID 1760485 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[N:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:28][CH:27]=1.[C:50]1([CH:56]([C:67]([O-])=[O:68])[C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[C:35]([N:34]=[C:33]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[NH:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:67](=[O:68])[CH:56]([C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[CH:31][CH:30]=1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22140016Monobenzyl 2-phenylmalonateHCID 178454281HCID 178454281, compound

Product 1

HCID 178454282HCID 178454282, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBTU (88 mg; 0.274 mmol) was added to a solution of 1-[4-(aminomethyl)phenyl]-2,3-di-tert-butyloxycarbonyl-guanidine hydrochloride (8) (100 mg; 0.249 mmol), monobenzyl 2-phenylmalonate (67.3 mg; 0.249 mmol), HOBt (37 mg; 0.274 mmol) and triethylamine (104 μl; 0.747 mmol) in DMF (5 ml), and the solution was stirred at room temperature overnight. After stripping off the solvent under reduced pressure, the residue was taken up in ethyl acetate (20 ml) and washed 3× with 5% NaHCO3 solution, 3× with 0.5 M HCl and 1× with saturated NaCl solution. The organic phase was dried (Na2SO4) and the solvent was stripped off under reduced pressure. The product was recrystallized from ethanol/water.

Workup

  1. washwashed 3× with 5% NaHCO3 solution, 3× with 0.5 M HCl and 1× with saturated NaCl solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customThe product was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-00a1eb0230904c969e36548bd9e17302
Source dataset
uspto-grants-2005_01
Patent number
US06841702B2

Reaction notes

Loading…