Lithium diisopropylamide → 3-Cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid ethyl ester

HRID 505587

Reaktionsgleichung

Reaktionsgleichung von HRID 505587
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][C:16](=[O:18])[CH3:17])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[Li+].CC([N-]C(C)C)C.[CH:28]1([CH2:33]I)[CH2:32][CH2:31][CH2:30][CH2:29]1>COC1SC(=O)N(CSP(OC)(OC)=S)N=1.C1COCC1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:6]1[CH:7]=[CH:8][C:9]([S:12]([CH2:15][C:16](=[O:18])[CH3:17])(=[O:14])=[O:13])=[CH:10][CH:11]=1)[CH2:33][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 2762531(Iodomethyl)cyclopentaneHCID 67485521[4-(2-Oxo-propylsulfonyl)-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 674858383-Cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 13709MethidathionLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of the title B compound, [4-(2-oxo-propylsulfonyl)-phenyl]-acetic acid ethyl ester (8 g, 0.028 mol) in 5 mL of DMTP and 80 mL of THF is cooled to −78 g and then treated with 15 mL of LDA (2 M solution in THF/hexane, 0.030 mol). The reaction is maintained at −78° C. for 20 min and then treated with a solution of 5.91 g (0.028 mL) of cyclopentylmethyl iodide in a mixture of THF (10 mL) and DMTP (3 mL), and the reaction is maintained at −78° C. for 6 h and subsequently at RT for another 6 h. The reaction is quenched with saturated ammonium chloride solution (20 mL). The organic layer is separated and aqueous layer then extracted with ethyl acetate (2×50 mL). Both the organic layers are combined and then washed with water. The organic layer is dried over sodium sulfate, filtered and evaporated under vacuum to give a brown oil as a crude product which is purified by column chromatography over Silica gel (60-120 mesh) using 80/20—hexane/ethyl acetate as an eluent to give 3-cyclopentyl-2-[4-(2-oxo-propylsulfonyl)-phenyl]-propionic acid ethyl ester as a white solid.

Aufarbeitung

  1. temperaturethe reaction is maintained at −78° C. for 6 h and subsequently at RT for another 6 h
  2. customThe reaction is quenched with saturated ammonium chloride solution (20 mL)
  3. customThe organic layer is separated
  4. extractionaqueous layer then extracted with ethyl acetate (2×50 mL)
  5. washwashed with water
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customto give a brown oil as a crude product which
  10. customis purified by column chromatography over Silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-069c0291476949ad9ff543b06405c1c6
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781451B2

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