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

HRID 726718Notes

Reaction equation

HRID 726718 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=2)[C:13]([NH:15][CH:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[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:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][CH:31]=2)[C:13]([NH:15][CH:16]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][C:18]([OH:20])=[O:19])=[O:14])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86751963Ethyl beta-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]3-pyridine-propanoate

Product 1

HCID 67841335beta-[[3-[4-(Aminoiminomethyl)benzyl]aminobenzoyl]amino]-3-pyridinepropanoic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl β-[[3-[4-(aminoiminomethyl)benzyl]aminobenzoyl]amino]3-pyridine-propanoate (0.35 g; 0.8 mmoles) 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 290 mg of white material. FAB-MS: MH+ =418.0.

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-7868883c590c49b283e7d225b3141d68
Source dataset
uspto-grants-1998_01
Patent number
US05710166

Reaction notes

Loading…