Triethylamine → 2-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl ester

HRID 1061623

Reaktionsgleichung

Reaktionsgleichung von HRID 1061623
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](O)=[O:39])=[CH:33][CH:32]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:13][N:12]1[C:38](=[O:39])[CH2:37][C:34]1[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 207247484-(2,2-Dimethylpropionyloxy)pyrazolidine-1-carboxylic acid 1-benzyl ester

Produkt 1

HCID 207247472-[2-(4-Fluorophenyl)acetyl]-4-(2,2-dimethylpropionyloxy) pyrazolidine-1-carboxylic acid 1-benzyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(2,2-Dimethylpropionyloxy)-pyrazolidine-1-carboxylic acid 1-benzyl ester, 30,(1.45 g, 4.23 mmol) is dissolved in dichloromethane (21 mL). The solution is cooled to 0° C. and triethylamine (1.30 mL, 9.31 mmol) added dropwise via syringe. The cold bath is removed and the reaction allowed to warm to room temperature and continue stirring 20 minutes. 4-Fluorophenylacetic acid (848 mg, 5.50 mmol) is added. After stirring for 5 minutes, the reaction mixture is transferred via cannula into a solution of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrogen chloride in dichloromethane (21 mL) maintained at 0° C. The reaction is allowed to stir and gradually warm to room temperature over 12 hours. The reaction is washed with a 5% aqueous solution of Na2CO3 (2×50 mL). The combined aqueous layers are extracted several times with dichloromethane (50 mL) and the combined organic layers washed with brine, dried, filtered and concentrated in vacuo. The crude product is purified over silica (2:1 to 1:1 hexane/ethyl acetate) to afford 1.71 g (91% yield) of the desired product as a white solid.

Aufarbeitung

  1. customThe cold bath is removed
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for 5 minutes
  4. temperaturemaintained at 0° C
  5. stirringto stir
  6. temperaturegradually warm to room temperature over 12 hours
  7. washThe reaction is washed with a 5% aqueous solution of Na2CO3 (2×50 mL)
  8. extractionThe combined aqueous layers are extracted several times with dichloromethane (50 mL)
  9. washthe combined organic layers washed with brine
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe crude product is purified over silica (2:1 to 1:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f90d2720f8ab4db0acb19cb4e25d4cad
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960593B2

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