Water → methyl (S)-2-tert-butoxycarbonylamino-5-(3,4-difluorophenyl)-5-oxopentanoate

HRID 553889

Reaktionsgleichung

Reaktionsgleichung von HRID 553889
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].O.[F:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[F:26]>O1CCCC1>[C:14]([O:13][C:11]([NH:6][C@@H:5]([CH2:9][CH2:8][C:7]([C:23]1[CH:22]=[CH:21][C:20]([F:19])=[C:25]([F:26])[CH:24]=1)=[O:10])[C:3]([O:2][CH3:1])=[O:4])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 962WaterHCID 108684851-O-tert-butyl 2-O-methyl (2S)-5-oxopyrrolidine-1,2-dicarboxylateHCID 178505835HCID 178505835, Verbindung

Produkt 1

HCID 67458709methyl (S)-2-tert-butoxycarbonylamino-5-(3,4-difluorophenyl)-5-oxopentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.5 g) in tetrahydrofuran (100 mL), 3,4-difluorophenylmagnesium bromide (0.5 M solution in tetrahydrofuran; 50 mL) was added dropwise at −40° C. over 10 minutes, and the reaction solution was stirred at −40° C. to 0° C. for two hours. Water was added to the solution in small portions, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 8.0 g of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-e8292d5e9c7d49339f2a46ec3d292f80
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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