Sodium Hydroxide → Acetate

HRID 2396614Notes

Reaction equation

HRID 2396614 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=3[CH2:8][N:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:10][C:4]2=[N:3][N:2]=1.[OH-].[Na+]>C(O)C>[CH:1]1[N:5]2[C:6]3[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=3[CH2:8][N:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:10][C:4]2=[N:3][N:2]=1.[C:13]([O-:15])(=[O:14])[CH3:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19700581HCID 19700581, compound

Product 2

HCID 175AcetateHCID 19700581HCID 19700581, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-5(6H)-propanoic acid, 8-[[4-(iminoaminomethyl)phenyl]methoxy]-1-methyl-6-oxo, ethyl ester in 3 mL ethanol at room temperature was added 0.75 mL 2N sodium hydroxide and the reaction stirred for 45 mins. The mixture was quenched 0.5 mL glacial acetic acid and purified by HPLC (solvent gradient 1:4 acetonitrile:water(0.5% acetic acid) (time 0 to 10 mins.) to 3:2 acetonitrile:water(0.5% acetic acid) (time 50 mins.), 20 mL/min, C18 2" column, Rf =33.2 mins.) to yield 4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-5(6H)-propanoic acid, 8-[[4-(iminoaminomethyl)phenyl]methoxy]-1-methyl-6-oxo, acetate. Exact mass (FAB, MH+) cald for C22H23N6O4 : 435.1781, found 435.1744.

Workup

  1. customThe mixture was quenched 0.5 mL glacial acetic acid
  2. custompurified by HPLC (solvent gradient 1:4 acetonitrile:water(0.5% acetic acid) (time 0 to 10 mins.) to 3:2 acetonitrile:water(0.5% acetic acid) (time 50 mins.), 20 mL/min, C18 2" column, Rf =33.2 mins.)

Sources & evidence

ORD record
ord-28720ee8d832452b93c8b746bf15b69d
Source dataset
uspto-grants-1996_02
Patent number
US05493020

Reaction notes

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