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

HRID 1844708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844708
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 708691941-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acidAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e71df508eb1f48b590385f378e248ca5
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946446B2

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