Diisopropylethylamine → HCID 86751964, compound

HRID 726720Notes

Reaction equation

HRID 726720 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].Cl.Cl.[NH2:18][CH:19]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C([N:35](CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[NH2:35][N:2]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][CH2:9][CH2:10][C:11]([NH:18][CH:19]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:13])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 167699873-[4-Cyanobenzyl]aminopropanoic acidHCID 22608516Ethyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride

Product 1

HCID 86751964HCID 86751964, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[4-cyanobenzyl]aminopropanoic acid (0.41 g; 2 mmoles), ethyl βamino-β-(3-pyridyl)-propanoate dihydrochloride (0.46 g; 1.7 mmoles), N,N-diisopropylethylamine (0.52 g; 4 mmoles) and benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.88 g; 2 mmoles) were stirred in N,N-dimethylformamide (25 ml) at room temperature for 1 hr. The reaction mixture was taken down to dryness and the residue was purified by HPLC. The lyophilized product was redissolved in ethanol (30 ml). The solution was saturated with HCl gas and allowed to stir overnight. The mixture was taken down to dryness and the residue was redissolved in ethanol (20 ml). To this solution, ammoniumchloride (1 g) and ammonium hydroxide (10 ml) were added. The reaction mixture was stirred at room temperature for 4 hrs and the solvent was removed under reduced pressure. The residue was purified by HPLC using acetonitrile/water/trifluoroacetic acid system. The desired fractions were collected and lyophilized to give 460 mg of white material (57% yield). FAB-MS: MH+ =398.2.

Workup

  1. customthe residue was purified by HPLC
  2. dissolutionThe lyophilized product was redissolved in ethanol (30 ml)
  3. dissolutionthe residue was redissolved in ethanol (20 ml)
  4. additionTo this solution, ammoniumchloride (1 g) and ammonium hydroxide (10 ml) were added
  5. stirringThe reaction mixture was stirred at room temperature for 4 hrs
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by HPLC
  8. customThe desired fractions were collected

Sources & evidence

ORD record
ord-16cecf09b77f4ce88228b43a673e01d1
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

Loading…