Allyl iodide → HCID 90067174, Verbindung

Allyl iodide (130 μl, 1.422 mmol) and sodium hydride (16.0 mg, 0.400 mmol) were added to a stirred solution of (3R,3aR,6R,6aR)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydro-furo[3,2-b]furan-3-ol (82.8 mg, 0.143 mmol) in DMF (1.4 ml). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between EtOAc (75 ml), water (20 ml), and 2 N HCl (10 ml). The organic layer was washed with water (2×30 ml, brine was added to each wash to break an emulsion) and brine (1×20 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give an amber residue. Flash chromatography of the residue utilizing a 4 g silica RediSep Rf® column and employing a 0-40% EtOAc/hexane gradient followed by 40% EtOAc/hexane afforded the title compound as a pale yellow solid. LC-MS: calculated for C33H38ClN3O5Si 619.23 observed m/e: 620.32 (M+H)+ (Rt 1.43/2 min).

1. customThe reaction mixture was partitioned between EtOAc (75 ml), water (20 ml), and 2 N HCl (10 ml)
2. washThe organic layer was washed with water (2×30 ml, brine
3. additionwas added to
4. washeach wash
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customto give an amber residue

ORD-Eintrag

ord-c180730f0ca9435392857bd023991be0

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290517B2