Lithium Hydroxide → beta-[[3-[4-(Aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoic acid

HRID 726716Notes

Reaction equation

HRID 726716 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][NH:9][C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:14])=[CH:6][CH:5]=1.[OH-].[Li+]>CO>[NH2:1][N:2]=[CH:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][NH:9][C:10]2[CH:11]=[C:12]([CH:23]=[CH:24][CH:25]=2)[C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86751962Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoate

Product 1

HCID 67841149beta-[[3-[4-(Aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl β-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]propanoate (75 mg) was treated with 1N lithium hydroxide and methanol (1:1; 20 ml) for 5 min. Methanol was removed under reduced pressure and the residue was purified by HPLC using acetonitrile/water/trifluoroacetic acid system. The desired fractions were collected and lyophilized to give 66 mg of white material. FAB-MS: MH+ =341.2.

Workup

  1. customMethanol was removed under reduced pressure
  2. customthe residue was purified by HPLC
  3. customThe desired fractions were collected

Sources & evidence

ORD record
ord-a5d97884ccdf49d8896e33161ee45d87
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

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