(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) → (S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate

HRID 453706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453706
C([C@@H]([O-])[C@@H](C(O)=O)[O-])(O)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@@H:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1>CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C@@H:19]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])=[CH:14][CH:13]=1

Komponenten

3

Edukt 1

HCID 86660298(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate)

Produkt 1

HCID 58556882(S)-((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetateAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (1S,2S)-1,2-dicarboxyethane-1,2-bis(olate) (diastereomer 2 of 18) (150 mg, 0.35 mmol) was dissolved in EtOAc (50 ml) and washed with a satured Na2CO3 solution (25 ml). The organic phase was dried over Na2SO4, and the solvent was removed in vacuo giving (S)—((R)-quinuclidin-3-yl) 2-(4-fluorophenylamino)-2-phenylacetate (60.0 mg, 0.17 mmol). This compound was dissolved in acetonitrile (2.5 ml), and 2-bromo-1-(4-hydroxyphenyl)-ethanone (36.0 mg, 0.17 mmol) was added. The reaction mixture was stirred at r.t. for 24 hours. The solvent was removed under vacuum and crude was purified by preparative HPLC to afford (R)-3-((S)-2-(4-fluorophenylamino)-2-phenylacetoxy)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane 2,2,2-trifluoroacetate (23.5 mg, 23% yield).

Aufarbeitung

  1. washwashed with a satured Na2CO3 solution (25 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c6ca8e8de3cd47c89e6654e0dbd2c22a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492548B2

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