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DL-cysteine → 2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)-4,5-dihydrothiazole-4-carboxylic acid

HRID 1750450
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750450
[OH-].[Na+].[C:3]([N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:10]([C:19]#[N:20])[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4].N[CH:22]([C:25]([OH:27])=[O:26])[CH2:23][SH:24]>C(O)C>[C:3]([N:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[C:10]([C:19]2[S:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[N:20]=2)[CH:9]=[N:8]1)([CH3:6])([CH3:5])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 594DL-cysteine3×HCID 14798Sodium Hydroxide3×HCID 867212891-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

Produkt 1

HCID 867212902-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)-4,5-dihydrothiazole-4-carboxylic acidAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixed solution of 1N aqueous sodium hydroxide solution (2.65 ml, 2.65 mmol) of the compound (430 mg, 1.77 mmol) obtained in step 1 and DL-cysteine (321 mg, 2.65 mmol), and ethanol (5.3 mL) was stirred at 80° C. for 3 hr. DL-cysteine (200 mg) and 1N aqueous sodium hydroxide solution (1.5 mL) were further added thereto, and the mixture was stirred at 80° C. for 14 hr. DL-cysteine (321 mg) and 1N aqueous sodium hydroxide solution (2.65 mL) were further added thereto, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid and ethyl acetate were added thereto. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate and diethyl ether to give 2-(1-(tert-butyl)-5-(4-fluorophenyl)-1H-pyrazol-4-yl)-4,5-dihydrothiazole-4-carboxylic acid (385 mg, 1.108 mmol, 62.7%) as a pale-yellow powder.

Aufarbeitung

  1. stirringthe mixture was stirred at 80° C. for 5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid and ethyl acetate
  3. additionwere added
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d08df801ffcc432ebbeb33d9550ca9db
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156837B2

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