Reaktion #48842

Reaktionsgleichung

3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide

Triethylamine

triethylsilane

→

desired compound

Ausbeute 21.4%

3-Hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methyl-1,3-thiazol-2-yl)benzamide

Ausbeute 21.4%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for a further 48 hours
2. 2
   FiltrationThe reaction was filtered through celite
3. 3
   Einengenthe filtrate concentrated in vacuo
4. 4
   Sonstigeto give a residue which
5. 5
   Sonstigewas chromatographed on silica
6. 6
   Wascheneluting with a gradient of 50-100% ethyl acetate in isohexane

Vorschrift

Triethylamine (0.11 mL, 0.79 mmol) and triethylsilane (4.88 mL, 27.3 mmol) were added to palladium (11) acetate (56 mg, 9 mol %) in DCM (14 mL) under an atmosphere of argon. The reaction was stirred for 15 mins then 3-(benzyloxy)-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methyl-1,3-thiazol-2-yl)benzamide (1.4 g, 2.73 mmol) in DCM (14 mL) added dropwise and stirred for a further 48 hours. The reaction was filtered through celite and the filtrate concentrated in vacuo to give a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (0.18 g).

Quelle