Propionic Acid → HCID 59094512, compound

Temperature

60 °C

A solution of (3aR,4R,6R,6aR)-N′-hydroxy-6-methoxy-2,2-dimethyl tetrahydrofuro[3,4-d][1,3]dioxole-4-carboximidamide (Preparation 35) (1.1 g, 4.74 mmol), propionic acid (0.39 g, 5.27 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 g, 5.74 mmol) in diethylene glycol dimethyl ether (10 ml) was heated under reflux at 60° C. for twelve hours and then heated at 110° C. for a further 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water (50 ml) and a mixture of ether (25 ml) and pentane (25 ml). The organic phase was separated and the aqueous layer was extracted with more ether/pentane mixture (50 ml). The combined organic extracts were dried (anhydrous magnesium sulphate) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of diethyl ether:pentane (1:2 by volume) gradually changing to diethyl ether:pentane (1:1 by volume) to give the title compound (0.87 g).

1. temperatureheated at 110° C. for a further 3 hours
2. customThe solvent was evaporated under reduced pressure
3. customthe residue was partitioned between water (50 ml)
4. additiona mixture of ether (25 ml) and pentane (25 ml)
5. customThe organic phase was separated
6. extractionthe aqueous layer was extracted with more ether/pentane mixture (50 ml)
7. dry with materialThe combined organic extracts were dried (anhydrous magnesium sulphate)
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of diethyl ether:pentane (1:2 by volume)

ORD record

ord-27a841c64c994a4d8fa1402daf43d9bb

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624158B2