Hydrochloric Acid → Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoate

HRID 726715Notes

Reaction equation

HRID 726715 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:20]([O:22][C:23](=[O:27])[CH2:24][CH2:25][NH2:26])[CH3:21].Cl.C([N:32](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.[Cl-].[NH4+].[OH-].[NH4+]>CN(C)C=O.C(O)C>[NH2:32][N:2]=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([NH:26][CH2:25][CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:27])=[O:14])=[CH:18][CH:19]=1

Participants

10

Reactant 7

HCID 313Hydrochloric Acid2×HCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 419889Ethyl 3-aminopropanoateHCID 197073993-[4-Cyanobenzyl]aminobenzoic acid

Product 1

HCID 86751962Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

3-[4-cyanobenzyl]aminobenzoic acid (0.25 g; 1 mmol), β-alanine ethyl ester.HCl (0.15 g; 1 mmol), N,N-diisopropylethylamine (0.26 g; 2 mmoles) and benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.44 g; 1 mmol) 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 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, ammonium chloride (1 g) and ammonium hydroxide (10 ml) were added. The reaction mixture was stirred at room temperature overnight 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 190 mg of white material. FAB-MS: MH+ =369.5

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by HPLC
  4. customThe desired fractions were collected

Sources & evidence

ORD record
ord-7cabe7f0fa1240cb939f9cdd23059fa5
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

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