Lithium Hydroxide → 1-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acid

HRID 1844708Notes

Reaction equation

HRID 1844708 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([S:14](=[O:20])(=[O:19])[NH:15][CH:16]3[CH2:18][CH2:17]3)[CH:10]=[C:9]2[C:21]([O:23]CC)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>CO.O>[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([S:14](=[O:20])(=[O:19])[NH:15][CH:16]3[CH2:17][CH2:18]3)[CH:10]=[C:9]2[C:21]([OH:23])=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70869105Ethyl 1-(cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 708691941-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acidYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 3a (8.0 g, 22.0 mmol) in MeOH (200 mL) was added a solution of LiOH (4.2 g, 100 mmol) in water (50 mL) and the solution was warmed to 50° C. overnight, cooled to rt and concentrated. The residue was diluted with water and acidified to pH˜4 with 4N aq. HCl and the solution was extracted with EA twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=2/1) to give compound 3b (6.0 g, 80%) as a white solid.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionthe solution was extracted with EA twice
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by CC (PE/EA=2/1)

Sources & evidence

ORD record
ord-e71df508eb1f48b590385f378e248ca5
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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