Sodium Hydroxide → HCID 19742811, compound

HRID 893602Notes

Reaction equation

HRID 893602 reaction equation
[C:1]([NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]([C:31]([O:33]C)=[O:32])=[C:29]([Cl:35])[N:28]=[C:27]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:21][CH:20]=1)(=[O:12])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[C:1]([NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[C:30]([C:31]([OH:33])=[O:32])=[C:29]([Cl:35])[N:28]=[C:27]2[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:21][CH:20]=1)(=[O:12])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44376822HCID 44376822, compound

Product 1

HCID 19742811HCID 19742811, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 1-((2'-((benzoylamino)sulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid, methyl ester (25 mg, 0.044 mmol) in methanol (1.0 ml) was added 2N sodium hydroxide solution (0.50 ml). The pale yellow solution was stirred at room temperature for 3 hours then the methanol was removed in vacuo. Saturated sodium dihydrogen phosphate solution was added followed by ethyl acetate and the organic phase separated. The aqueous phase was re-extracted twice with ethyl acetate, then the combined organic phase washed with brine, dried, (magnesium sulfate) and the solvent removed in vacuo. Flash chromatography (silica gel, 0.25% acetic acid-2.5% methanolmethylene chloride) afforded 1-((2'-((benzoylamino)sulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid (11.5 mg, 47%) as a white solid; 1H NMR (300 MHz, CD3OD) δ8.27 (d, J=8.5 Hz, 1H), 7.71-7.50 (m, 3H), 7.50-7.36 (m, 4H), 7.35-7.23 (m, 3H), 6.98 (d, J=8.0 Hz, 2H), 5.70 (s, 2H), 2.67 (apparent t, 2H), 1.64 (apparent quin, 2H), 1.35 (apparent sext, 2H), 0.90 (t, J=7.3 Hz, 3H); FAB-MS: 574 (M+Na), 552 (M+H).

Workup

  1. customthe methanol was removed in vacuo
  2. additionSaturated sodium dihydrogen phosphate solution was added
  3. customthe organic phase separated
  4. extractionThe aqueous phase was re-extracted twice with ethyl acetate
  5. washthe combined organic phase washed with brine
  6. customdried
  7. custom(magnesium sulfate) and the solvent removed in vacuo

Sources & evidence

ORD record
ord-80122768ea054bfca6049e1c71f7afe0
Source dataset
uspto-grants-1992_06
Patent number
US05126342

Reaction notes

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