Tetrabutylammonium Fluoride → (4S,5S)-tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-4-((5-propylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

HRID 1009118

Reaktionsgleichung

Reaktionsgleichung von HRID 1009118
[Si]([C:8]1[S:9][C:10]([CH2:37][CH2:38][CH3:39])=[C:11]([CH2:13][C@H:14]2[C@@H:18]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[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(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:20][CH2:19][C@H:18]1[O:17][C:16]([CH3:29])([CH3:28])[N:15]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[C@H:14]1[CH2:13][C:11]1[N:12]=[CH:8][S:9][C:10]=1[CH2:37][CH2:38][CH3:39]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67304570(4S,5S)-tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 59347039(4S,5S)-tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-4-((5-propylthiazol-4-yl)methyl)oxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4S,5S)-Tert-butyl 4-((2-(tert-butyldimethylsilyl)-5-propylthiazol-4-yl)methyl)-5-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate was dissolved in THF (3 mL) and cooled to 0° C. when TBAF (0.808 ml, 0.808 mmol) was added. The reaction was stirred one hour before being 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.

Aufarbeitung

  1. additionwas added
  2. custombefore being quenched with saturated ammonium chloride
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-5629902611ee45aabf5b9f5e0c27346a
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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