Phosphorus oxychloride → HCID 69827775, compound

Temperature

0 °C

To a solution of (3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyl-N-(2-oxobutyl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (740 mg) in dry toluene (10 ml), under nitrogen was added phosphorous oxychloride (1.44 ml) and the mixture was heated under reflux for 3.5 h. The reaction mixture was cooled to 0° C., quenched with saturated aqueous sodium bicarbonate (30 mls), stirred vigorously for 30 min and extracted with ethyl acetate (4×50 ml); the organic layers were combined, washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo to give a crude product, which was purified by flash column chromatography on silica gel, eluting with a mixture of 5:1 to 7:2 cyclohexane:ethyl acetate, to give the title compound as a yellow oil (0.83 g).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 3.5 h
3. customquenched with saturated aqueous sodium bicarbonate (30 mls)
4. extractionextracted with ethyl acetate (4×50 ml)
5. washwashed with brine (30 ml)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto give a crude product, which
9. customwas purified by flash column chromatography on silica gel
10. washeluting with a mixture of 5:1 to 7:2 cyclohexane

ORD record

ord-a8175d6a6fa84cd3aac412b0a8e39e49

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677316B2