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

HRID 1799361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799361
[C:1]12([NH:11][C:12]([C:14]3[CH:15]=[N:16][N:17]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)[C:18]=3[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+]>CO>[C:1]12([NH:11][C:12]([C:14]3[CH:15]=[N:16][N:17]([C:23]4[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)[C:18]=3[S:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59516107Methyl 4-[4-(1-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate2×

Produkt 1

HCID 250055794-[4-(1-Adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 4-[4-(1-adamantylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (143 mg, 0.32 mmol) (Intermediate #3) was dissolved in methanol and treated at ambient temperature with 2M aqueous sodium hydroxide solution. The mixture was stirred at ambient 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 compound as a white solid (132 mg, 94%).

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-43fec1819daf4f64be87b79044d8a794
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344016B2

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