Sodium Hydroxide → HCID 71203601, compound

HRID 1844559Notes

Reaction equation

HRID 1844559 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([C:19]2[N:23]([CH3:24])[C:22]([C:25]([O:27]C)=[O:26])=[CH:21][C:20]=2[CH3:29])=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([C:19]2[N:23]([CH3:24])[C:22]([C:25]([OH:27])=[O:26])=[CH:21][C:20]=2[CH3:29])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71203612HCID 71203612, compound

Product 1

HCID 71203601HCID 71203601, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Methyl 5-(6-methoxy-4′-sulfamoyl-[1,1′-biphenyl]-3-yl)-1,4-dimethyl-1H-pyrrole-2-carboxylate (step-2, 0.77 g, 1.85 mmol) was suspended in ethanol (15 ml), to this was then added aqueous solution of NaOH (0.37 g. 9.29 mmol in 5 ml water) at 0° C. The reaction mixture was stirred at 25° C. for 15 hours. The progress of the reaction was monitored by TLC. The reaction mixture was concentrated under reduced pressure. The residue obtained after concentration was then dissolved in water (10 ml) and dilute hydrochloric acid was added to the mixture so obtained to bring the pH of the mixture to between 6 and 7. The mixture was then extracted with ethyl acetate (2×50 ml). The separated combined organic layer was then dried over anhydrous sodium sulfate. The solvent was evaporated from the dried organic layer under reduced pressure to obtain the title compound 10c (0.71 g, 95.9%).

Workup

  1. customat 0° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. concentrationafter concentration
  5. dissolutionwas then dissolved in water (10 ml)
  6. additiondilute hydrochloric acid was added to the mixture
  7. customso obtained
  8. extractionThe mixture was then extracted with ethyl acetate (2×50 ml)
  9. dry with materialwas then dried over anhydrous sodium sulfate
  10. customThe solvent was evaporated from the dried organic layer under reduced pressure

Sources & evidence

ORD record
ord-e8f3d0915be4469b9e9482f31de10d61
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

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