Sodium Hydroxide → 5-n-Butyl-2-(5-carboxy-2-chlorophenyl)-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36270Notes

Reaction equation

HRID 36270 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:47])(=[O:46])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:25][CH:24]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35](=[O:46])(=[O:47])[NH:36][C:37](=[O:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:44])=[CH:27][CH:28]=2)[C:7](=[O:21])[N:8]([C:10]2[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=2[Cl:20])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 103724973-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-benzoic acid methyl ester

Product 1

HCID 117651285-n-Butyl-2-(5-carboxy-2-chlorophenyl)-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 84%

Procedure

A solution of 71 mg (0.102 mmole) of 5-n-butyl-2-[5-(carbomethoxy)-2-chlorophenyl]-4-[[2'-[N-(2-chlorobenzoyl)-sulfamoyl]-biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 65, Step D) in 0.7 mL (0.7 mmole) of 1N NaOH (methanolic) was stirred at 60° C. overnight and then concentrated to dryness. The residue was dissolved in 1 mL of methanol, acidified to approximately pH 1.5 by addition of 1N HCl (methanolic), and again concentrated. The residue was dissolved in CHCl3, dried over Na2SO4, and filtered through Celite. Evaporation of the solvent yielded 58 mg (84%) of the title compound as a white solid; nearly homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 679 (M+1)+.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in 1 mL of methanol
  3. additionacidified to approximately pH 1.5 by addition of 1N HCl (methanolic)
  4. concentrationagain concentrated
  5. dissolutionThe residue was dissolved in CHCl3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through Celite
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f30de52a8a794d1fa33ee1a40884c2d8
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

Loading…