Dimethoxymethane → HCID 45277063, Verbindung

400 ml of a solution of a sodium tetraborate buffer solution (0.05 M) in a 0.4 mM disodium ethylenediaminetetraacetate aqueous solution, 0.648 g of tetrabutylammoniumbisulfate (1.91 mmol) and 11.1 g of 1,2:4,5-di-O-isopropylidene-β-D-erythro-2,3-hexodiuro-2,6-pyranose (43.0 mmol) were added to 10.1 g of (2R,4E)-6-benzyloxy-2-methylhex-4-enoic acid obtained in Example (76b) (43.2 mmol) in a mixed solvent of acetonitrile (167 ml) and dimethoxymethane (333 ml) at room temperature, and the mixture was stirred for 10 minutes. The reaction mixture was cooled in an ice bath. Then, a solution of 36.7 g of Oxone(trade mark) (59.6 mmol) in a 0.4 mM disodium ethylenediaminetetraacetate aqueous solution (200 ml) and a solution of 34.3 g of potassium carbonate (247 mmol) in water (200 ml) were separately added dropwise over eight hours. The mixture was stirred at the same temperature for one hour and then diluted with 100 ml of water, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1-1/1) to obtain 7.82 g of the title compound (total yield over two steps: 72%).

1. temperatureThe reaction mixture was cooled in an ice bath
2. stirringThe mixture was stirred at the same temperature for one hour
3. extractionfollowed by extraction with ethyl acetate
4. washThen, the organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationAfter filtration
7. customthe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1-1/1)

ORD-Eintrag

ord-ddb7bb318f984ec398cb0b4d4e13e265

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08158790B2