Dicyclohexylcarbodiimide → (2-acetyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

HRID 1255029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1255029
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][CH:27]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:28]([OH:30])=[O:29])(=[O:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@@H:49](O)[CH2:48]2>C1COCC1>[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@@H:49]([O:29][C:28](=[O:30])[CH:27]([NH:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17](=[O:19])[CH3:18])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:48]2

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67424703(2-Acetyl-phenylamino)-phenyl-acetic acid hydrochloride

Produkt 1

HCID 46840711(2-acetyl-phenylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

PS-DCC (890 mg, 1.184 mmol, loading: 1.33 mmol/g) is suspended in dry THF (10 mL). (2-Acetyl-phenylamino)-phenyl-acetic acid hydrochloride (I63) (181 mg, 0.59 mmol), HOBt (181 mg, 1.18 mmol), and (R)-quinuclidin-3-ol (226 mg, 1.78 mmol) are added and the mixture is shaken at RT overnight. PS-DCC is filtered off and the filtrate is evaporated. The residue is dissolved in EtOAc and washed with sat. NaHCO3, water and brine, dried over Na2SO4, filtered and evaporated. The resulting crude oil is purified by flash chromatography (DCM/MeOH=9/1) to afford the title compound as a colorless oil (239 mg, quantitative yield, mixture of diastereoisomers).

Aufarbeitung

  1. filtrationPS-DCC is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with sat. NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude oil is purified by flash chromatography (DCM/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-c9cff036e205483fab009f36971b5205
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455646B2

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