Sodium Thiosulfate → HCID 59909746, Verbindung

A solution of tert-butyl(3R)-6-cyclohexyl-3-({[2-hydroxy-1-(methoxycarbonyl)propyl]amino}carbonyl)hexanoate (Preparation 171) (6.48 g, 15.69 mmol) in dichloromethane (60 ml) was treated with Dess-Martin periodinane [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] (7.32 g, 17.26 mmol) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. A solution of sodium thiosulphate (6 g in 50 ml water) and a saturated aqueous sodium hydrogen carbonate solution (50 ml) were then added to the mixture which was stirred for a further 10 minutes. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were sequentially washed with water and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (100:0 to 90:10) to afford the title compound as a colourless oil (4.86 g)

1. stirringwas stirred for a further 10 minutes
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane
4. washThe combined organic layers were sequentially washed with water and brine
5. dry with materialdried over anhydrous magnesium sulphate
6. filtrationfiltered
7. customthe solvent removed under reduced pressure
8. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (100:0 to 90:10)

ORD-Eintrag

ord-35e7e18bf2df4d369f4d24bfaa5decdb

Quelldatensatz

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07214694B2