Water → HCID 69242447, compound

Participants

Reaction Steps

To a mixture of Example 39A (1.88 g, 6.6 mmol) and triethylamine (0.92 mL, 6.6 mmol) in THF (20 mL) at 0° C. under nitrogen was added methanesulfonyl chloride (1.51 g, 13.2 mmol). The mixture was allowed to warm up to room temperature and stirred for 12 hours after which it was concentrated under reduced pressure, and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×30 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to provide a yellow liquid. The yellow liquid was taken up in 100 mL of dry DMF under nitrogen and tetrabutylammonium cyanide (5 g, 20 mmol) was added to the solution. The mixture was heated to 50° C. for 60 hours after which the mixture was poured into cold water and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (MgSO4), filtered, concentrated under reduced pressure and purified by flash silica gel chromatography eluting with 50% ethyl acetate/50% hexane to provide the titled compound. MS (DCI/NH3) m/e 294 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 1.43 (s, 5 H) 1.49 (s, 4 H) 1.86 (m, 2 H) 1.99 (m, 2 H) 2.03 (m, 1 H) 2.10 (m, 2 H) 3.40 (m, 2 H) 3.52 (m, 2 H) 3.69 (m, 1 H) 4.58 (m, 1 H) 4.65 (m, 1 H).

Provenance & Evidence