tert-Butyldimethylsilyl chloride → (4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 20020

Reaktionsgleichung

Reaktionsgleichung von HRID 20020
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:11]1[CH2:24][C:25]1[N:26]=[CH:27][S:28][CH:29]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>C1COCC1>[Si:35]([C:27]1[S:28][CH:29]=[C:25]([CH2:24][C@H:11]2[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[O:14][C:13]([CH3:15])([CH3:16])[N:12]2[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[N:26]=1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Komponenten

5

Edukt 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67270188(4S,5S)-tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 67304891(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylate (0.148 g, 0.334 mmol) in THF (3 mL) was cooled to −78° C. when n-butyllithium (2.5 M in hexanes)(0.160 ml, 0.401 mmol) was added dropwise. The solution was warmed to −50° C. for 40 minutes and then cooled to −78° C. TBS-Cl (0.0605 g, 0.401 mmol) in THF (2 mL) was added dropwise and the solution was allowed to slowly warm to 0° C. when it was quenched with saturated ammonium chloride. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine and dried over sodium sulfate to afford the title compound, which was used without further purification.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturecooled to −78° C
  3. temperatureto slowly warm to 0° C. when it
  4. customwas quenched with saturated ammonium chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-c2f7b6ab97934f8984e2b05a70857450
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745484B2

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