Methanesulfonyl chloride → HCID 131724409, compound

A 0° C. solution of Example 7A (1.04 g, 5.0 mmol), and N,N-diisopropylethylamine (1.1 mL, 6.5 mmol) in dichloromethane (20 mL) was treated with methanesulfonyl chloride (0.46 mL, 6.0 mmol), warmed to room temperature, stirred for 16 hours, diluted with hexanes (20 mL), filtered through a pad of silica gel (15 g) with 10% diethyl ether in hexanes, and concentrated. The concentrate was dissolved in DMF (10 mL), treated with tetrabutylammonium iodide (400 mg, 1.1 mmol), 15-crown-5 (100 mg, 0.40 mmol), and sodium azide (1.0 g, 15.4 mmol), heated to 100° C., and stirred for 16 hours. The mixture was diluted with ethyl acetate (100 mL), washed with water (15 mL) and brine (15 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 234 (M+H)+.

1. filtrationfiltered through a pad of silica gel (15 g) with 10% diethyl ether in hexanes
2. concentrationconcentrated
3. dissolutionThe concentrate was dissolved in DMF (10 mL)
4. temperatureheated to 100° C.
5. stirringstirred for 16 hours
6. washwashed with water (15 mL) and brine (15 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes

ORD record

ord-82e264f99266448aaf756c098b41a1d2

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504512B2