Sodium hydride → HCID 86605607, Verbindung

HRID 1994070

Reaktionsgleichung

Reaktionsgleichung von HRID 1994070
[H-].[Na+].[C:3]([Si:7]([CH3:17])([CH3:16])[O:8][C:9]1[CH:10]=[C:11]([SH:15])[CH:12]=[CH:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:18]([O:20][C:21]([C@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28](Cl)=[O:29])=[O:22])[CH3:19]>C1COCC1.C(OCC)(=O)C>[CH2:18]([O:20][C:21]([C@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]([S:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:17])[CH3:16])[CH:10]=1)=[O:29])=[O:22])[CH3:19]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 219768683-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenethiolHCID 86605608HCID 86605608, Verbindung

Produkt 1

HCID 86605607HCID 86605607, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of sodium hydride (0.25 g, 6.3 mmol) in anhydrous THF (20 mL) is added 3-(t-butyl-dimethyl-silanyloxy)-benzenethiol (1.3 g, 5.22 mmol) at RT. After 10 min, the title A compound, (R)-1-chlorocarbonyl-pyrrolidine-2-carboxylic acid ethyl ester (1.1 g, 5.22 mmol) is added and the reaction is stirred for 24 h. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 25% ethyl acetate in hexane to yield (R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenyl-sulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester as a clear oil.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe crude product is purified on a Biotage 40M column

Quellen und Nachweise

ORD-Eintrag
ord-63dac54499cf4f5886219bbcb17ac26d
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652061B2

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