1-Iodopropane → (4S,5S)-tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 1009117

Reaktionsgleichung

Reaktionsgleichung von HRID 1009117
[Si:1]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][C@H:14]2[C@@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[O:17][C:16]([CH3:29])([CH3:28])[N:15]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[CH3:38][CH2:39][CH2:40][CH2-].ICCC>C1COCC1>[Si:1]([C:8]1[S:9][C:10]([CH2:38][CH2:39][CH3:40])=[C:11]([CH2:13][C@H:14]2[C@@H:18]([CH2:19][O:20][Si:21]([C:24]([CH3:25])([CH3:27])[CH3:26])([CH3:23])[CH3:22])[O:17][C:16]([CH3:29])([CH3:28])[N:15]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:12]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 336431-IodopropaneHCID 61028n-Butyl lithiumHCID 67304891(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 67304570(4S,5S)-tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)thiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.150 g, 0.269 mmol) in THF (3 mL) was cooled to −78° C. when N-BUTYLLITHIUM (2.5 M in hexanes) (0.119 ml, 0.296 mmol) was added dropwise. The solution was warmed to −50° C. for 40 minutes and then cooled to −78° C. 1-Iodopropane (0.0549 g, 0.323 mmol) was added dropwise and the solution was allowed to slowly warm to −50° C. and stirred for 1 hr. The reaction was quenched with saturated ammonium chloride. The layers were separated and the aqueous layer was extracted with ethyl acetate. 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 for the next step.

Aufarbeitung

  1. additionwas added dropwise
  2. temperaturecooled to −78° C
  3. temperatureto slowly warm to −50° C.
  4. customThe reaction was quenched with saturated ammonium chloride
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-29aed395132342308ab4b5dea7a479e6
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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