Reaktion #1605935

Reaktionsgleichung

compound 2.7b

tert-Butyl ((1S,2S)-1-(furan-2-yl)-3-(2-hydroxy-2-methylpropoxy)-2-methylpropyl)(methyl)carbamate

sodium periodate

→

compound 2.7c

Ausbeute 89.5%

(2S,3S)-2-((tert-butoxycarbonyl)(methyl)amino)-4-(2-hydroxy-2-methylpropoxy)-3-methylbutanoic acid

Ausbeute 89.5%

Lösungsmittel

water CCl4 MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with ethyl acetate (3×5 ml)
2. 2
   WaschenCombined organic layer was washed with saturated aqueous NaHSO3 (25 ml), brine
3. 3
   Trocknendried with anhydrous sodium sulfate
4. 4
   Einengenconcentrated in vacuo

Vorschrift

To a solution of compound 2.7b (120.0 mg, 0.35 mmol) in water:CCl4:MeCN (3:2:3, 9.6 ml) at room temperature was added sodium periodate (451.0 mg, 2.1 mmol, 6.0 equiv) followed by ruthenium chloride (25.0 mg, 0.12 mmol, 0.34 equiv). After stirring for 45 minutes, the aqueous layer was extracted with ethyl acetate (3×5 ml). Combined organic layer was washed with saturated aqueous NaHSO3 (25 ml), brine, dried with anhydrous sodium sulfate, and concentrated in vacuo to give compound 2.7c (100.0 mg) which was used for the next step without further purification. MS m/z (M+Na) 342.2

Quelle