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Sodium Carbonate → (2R,4S)-4-Hydroxy-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl ester

HRID 455274
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 455274
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][NH:7]1)=[O:5].C([O-])([O-])=O.[Na+].[Na+].[N:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:23][CH:22]=1)=[C:19]=[O:20]>C1COCC1>[CH3:2][O:3][C:4]([C@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][N:7]1[C:19](=[O:20])[NH:18][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([F:31])([F:30])[F:32])=[CH:23][CH:22]=1)=[O:5]
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Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 44118802Methyl (2R,4S)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideHCID 539725321-Isocyanato-4-(2,2,2-trifluoro-ethoxy)-benzene

Produkt 1

HCID 70976230(2R,4S)-4-Hydroxy-1-[4-(2,2,2-trifluoro-ethoxy)-phenylcarbamoyl]-pyrrolidine-2-carboxylic acid methyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of (2R,4S)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester, hydrochloride (3 g, 16.57 mmol) in THF (15 mL) was added solid Na2CO3 (2.10 g, 19.88 mmol) and stirred for 15 min. To this mixture, freshly prepared 1-Isocyanato-4-(2,2,2-trifluoro-ethoxy)-benzene (4.3 g, 19.88 mmol) in THF (10 mL) was added and stirred for 2 h at room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was taken up in DCM and washed with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography over silica (5% MeOH in DCM) to yield 2.7 g (50%) of the title compound as a white solid. LC-MS: 363.2 [M+1]+.

Aufarbeitung

  1. stirringstirred for 2 h at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by column chromatography over silica (5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-93e972e0e1d24e799fb2da8e0852dafb
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497288B2

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