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Sodium hydride → HCID 67500771, Verbindung

HRID 1187777
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1187777
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:26][C:27]1[CH:28]=[CH:29][C:30]([CH:33](OS(C(F)(F)F)(=O)=O)[C:34]([F:37])([F:36])[F:35])=[N:31][CH:32]=1>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][CH:33]([C:30]3[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][N:31]=3)[C:34]([F:37])([F:36])[F:35])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 66705807HCID 66705807, VerbindungHCID 86664596HCID 86664596, Verbindung

Produkt 1

HCID 67500771HCID 67500771, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (150 mg, example 6b) in dry THF (0.2 ml) under an argon atmosphere was added sodium hydride (34 mg, 60% dispersion in mineral oil) and stirring was continued for 15 minutes. Trifluoro-methanesulfonic acid 1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl ester (182 mg) was then added and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed sequentially with water and with saturated brine. The organic phase was separated, dried over sodium sulphate, and concentrated in vacuo. The reside was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S)-4-(2-{4-[1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethylamino]-phenyl}-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (99 mg, 38%) as a yellow oil. MS (ISP): 560.1 ([{81Br}M+H]+), 558.1 ([{79Br}M+H]+).

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. washwashed sequentially with water and with saturated brine
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe reside was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0cdd725814be4df2ae59751e88b1e89d
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673950B2

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