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Hydrochloric Acid → [3,5-Dimethyl-1-(4-phenylacetyl-benzyl)-1H-pyrazol-4-yl]-acetic acid

HRID 1631925
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1631925
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:6]([CH3:27])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([OH:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[C:9]=1[CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+].Cl>ClCCl.O1CCOCC1.O>[CH3:27][C:6]1[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[C:9]([CH3:10])[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:17]=2)[N:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66707459{1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester2×

Produkt 1

HCID 58071788[3,5-Dimethyl-1-(4-phenylacetyl-benzyl)-1H-pyrazol-4-yl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Oxidation: {1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester (intermediate 15.1.2, 100 mg, 0.26 mmol) was dissolved in 4 ml dichloromethane, cooled to 0° C. and Dess-Martin periodinane (135 mg, 0.32 mmol) was added to the solution. After warming to room temperature, the mixture was stirred for 3 h. The solvent was evaporated under reduced pressure. Saponification: The ester intermediate (70 mg, 0.19 mmol) was dissolved in 2 ml dioxane and aqueous NaOH solution (0.37 ml, 1 M). After stirring for 2.5 h at 60° C. and dilution with water, aqueous HCl solution (0.39 ml, 1 M) was added. The mixture was extracted with ethyl acetate, and the organic layer was dried with MgSO4 and evaporated under reduced pressure. The residue was purified by preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

Aufarbeitung

  1. temperatureAfter warming to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. stirringAfter stirring for 2.5 h at 60° C.
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried with MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3)

Quellen und Nachweise

ORD-Eintrag
ord-e3d53b142d9d437297f6bce22508506f
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791272B2

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