Triethylamine → HCID 86760620, compound

Temperature

70 °C

To a stirred solution of the product from Step B (1.8 g, 7.6 mmol) in dichloromethane (10 mL) was added triethylamine (1.3 mL, 9.2 mmol) followed by methanesulfonyl chloride (0.72 mL, 9.2 mmol) at 0° C. After 30 min, ether (50 mL) was added followed by water (50 mL). The organic layer was separated and the aqueous was extracted with ether (2×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated. The residue was taken up in DMF (20 mL) and sodium azide (0.99 g, 15.2 mmol) was added. The reaction mixture was heated at 70° C. for 14 h, poured into water, and extracted with ether (3×50 mL). The combined extracts were washed with brine, dried and evaporated. The residue was purified by chromatography (silica, hexane to 10% ethyl acetate in hexane) to give an oil (1.75 g, 83%): MS (ES) m/z 274 (M+); 1H NMR (CDCl3) 8.22 (1H, s), 8.09 (1H, s), 7.84 (1H, d, J=1.2 Hz), 7.78 (1H, d, J=1.2 Hz), 4.45 (4H, m), 4.24 (1H, m), 1.46 (3H, t, J=7.2 Hz). 1.35 (3H, d, J=6.8 Hz).

1. customThe organic layer was separated
2. extractionthe aqueous was extracted with ether (2×50 mL)
3. washThe combined organic layers were washed with brine (30 mL)
4. customdried
5. customevaporated
6. extractionextracted with ether (3×50 mL)
7. washThe combined extracts were washed with brine
8. customdried
9. customevaporated
10. customThe residue was purified by chromatography (silica, hexane to 10% ethyl acetate in hexane)

ORD record

ord-288b878da8c44210b7a4672f948f406a

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439262B1