Sodium Hydroxide → 3-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

HRID 1160503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160503
[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([O:24]C)=[O:23])[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=3)[C:22]([OH:24])=[O:23])[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57857096Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate

Produkt 1

HCID 595160843-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 3-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (175 mg, 0.45), (Intermediate #12) was dissolved in methanol (10 mL), treated with 2M aqueous sodium hydroxide solution (1.125 mL) and stirred at ambient temperature for 18 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title product as a white solid. (115 mg, 65%)

Aufarbeitung

  1. customMethanol was removed by evaporation under reduced pressure
  2. additionthe clear solution diluted with water (25 ml)
  3. addition2M HCl was added to pH4
  4. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  5. washThe combined extracts were washed with water (2×10 mL) and brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-17cc34e7ef0a480c9d8060f5461e19ac
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816391B2

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