N,N'-Dimethylethylenediamine → (S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate

HRID 1805361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805361
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C@@:5]12[CH2:13][C:12]1([CH3:15])[CH3:14].[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21](Br)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C@@:5]3([CH2:13][C:12]3([CH3:15])[CH3:14])[C:6]2=[O:11])[CH:20]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateHCID 67230523(S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one

Produkt 1

HCID 58305358(S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of (R) and (S)-5′-fluoro-2,2-dimethylspiro[cyclopropane-1,3′-indolin]-2′-one (2 mmol) (prepared as in Example 100), methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate (682 mg, 2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford the title compound as white powder (480 mg, 80%) which was used for the next step without further purification.

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a45b143ce03e4bbd95ca59db818facf5
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354443B2

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