Dicyclohexylcarbodiimide → (1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl hex-5-enoate

Temperature

40 °C

A 50 ml two-necked round-bottom flask was flame dried and allowed to be cooled under nitrogen. (1S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol (1 g, 1.66 mmol) in 10 ml of DMF, 0.05 g (0.33 mmol) of DMAP, 0.21 g (1.83 mmol) of 5-hexenoic acid, and 0.41 g (2.00 mmol) of N,N′-dicyclohexylcarbodiimide were added to the reaction flask. The reaction mixture was heated at 40° C. for 24 hours. The reaction was quenched with 10 ml saturated aqueous sodium bicarbonate. The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography and then concentrated under reduced pressure to provide 1.05 g of the title compound (90.52% yield).

1. temperatureA 50 ml two-necked round-bottom flask was flame
2. customdried
3. temperatureto be cooled under nitrogen
4. customThe reaction was quenched with 10 ml saturated aqueous sodium bicarbonate
5. customseparated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe solid was filtered off
9. customorganic solvent was evaporated off under vacuum
10. customThe crude product was purified by chromatography
11. concentrationconcentrated under reduced pressure

ORD record

ord-3ddc97f407314a828f1dbdde4b8c97da

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115109B2