Hydrochloric Acid → HCID 46179378, compound

HRID 572252Notes

Reaction equation

HRID 572252 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:13]=3[C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=3[CH3:30])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-:31].[Na+].OO.Cl>CS(C)=O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:13]=3[C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:31])[NH2:29])=[CH:24][C:23]=3[CH3:30])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67175664HCID 67175664, compound

Product 1

HCID 46179378HCID 46179378, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of compound 3-(3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (180 mg, 0.98 mmol) and sodium hydroxide (80 mg, 2.0 mol) in DMSO (5 mL) was added 0.1 mL of 30% hydrogen peroxide, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized by 1N HCl to PH=5-6, concentrated, and purified by preparative HPLC to give 3-(3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (29 mg, yield 15.4%) as a solid.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-65d523f6a5ee416192d8170a7c652313
Source dataset
uspto-grants-2015_05
Patent number
US09029402B2

Reaction notes

Loading…