2-Bromothiazole → HCID 67269896, Verbindung

HRID 1697256

Reaktionsgleichung

Reaktionsgleichung von HRID 1697256
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[Si:12]([O:19][C@H:20]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])/[CH:21]=[N:22]/[S@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CCOCC>[Si:12]([O:19][C@H:20]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[C@@H:21]([NH:22][S@:23]([C:25]([CH3:26])([CH3:27])[CH3:28])=[O:24])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

Komponenten

5

Edukt 3

HCID 764302-BromothiazoleHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178418339Butyllithium

Produkt 1

HCID 67269896HCID 67269896, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 2-bromothiazole (7.9 ml, 89 mmol) in 200 mL ether was cooled to −78° C. and treated with a solution of n-butyllithium (36 ml, 89 mmol) (2.5N in hexanes). After stirring for 30 minutes the reaction mixture was slowly added to a cooled (−78° C.) suspension of (S,E)-N—((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (25.000 g, 59 mmol) in 100 mL ether. The reaction mixture was allowed to stir at −78° C. for one hour. The reaction mixture was quenched with MeOH and saturated NH4Cl solution. The organic solution was washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave (S)—N-((1R,2S)-2,3-bis(tert-butyldimethylsilyloxy)-1-(thiazol-2-yl)propyl)-2-methylpropane-2-sulfinamide (24.81 g, 83% yield).

Aufarbeitung

  1. additionwas slowly added to
  2. temperaturea cooled
  3. stirringto stir at −78° C. for one hour
  4. customThe reaction mixture was quenched with MeOH and saturated NH4Cl solution
  5. washThe organic solution was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-94bd15697fa24e409acd93184e48aa52
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163909B2

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