تفاعل #2286897
ord-21079d3b32ea41b5880f01dae755380b
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1أخرىpartitioned between ethyl acetate (150 mL) and water (50 mL)
- 2غسيلThe organic layer was washed with brine
- 3تجفيفa dried (Na2SO4)
- 4ترشيحfiltered
- 5تركيزconcentrated
- 6أخرىThe concentrate was purified by flash chromatography on silica gel with 5% ethyl acetate in hexanes
- 7أخرىto provide an intermediate which
- 8استخلاصextracted with ethyl acetate
- 9غسيلThe extract was washed with water and brine
- 10تجفيفdried (Na2SO4)
- 11ترشيحfiltered
- 12تركيزconcentrated
- 13أخرىThe concentrate was purified by reverse phase HPLC (C-18, 30 to 100% acetonitrile/water/0.1% TFA)
الإجراء التجريبي
To a mixture of EXAMPLE 47A (71 mg), 2-methyl-1-naphthol (35 mg), triphenylphosphine (58 mg) in THF (2 mL) and di-tert-butyl azodicarboxylate (55 mg) was stirred at ambient temperature overnight and partitioned between ethyl acetate (150 mL) and water (50 mL). The organic layer was washed with brine and a dried (Na2SO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel with 5% ethyl acetate in hexanes to provide an intermediate which was dissolved in THF (2 mL), methanol (1 mL) and water (1 mL) and hydrolyzed with LiOH (100 mg) overnight. The mixture was acidified with 5% HCl and extracted with ethyl acetate. The extract was washed with water and brine and dried (Na2SO4), filtered and concentrated. The concentrate was purified by reverse phase HPLC (C-18, 30 to 100% acetonitrile/water/0.1% TFA). 1H NMR (300 MHz, CDCl3) δ 8.74 (s, 1H), 8.12 (dd, 1H), 7.82 (d, 1H), 7.77 (d, 1H), 7.52 (d, 1H), 7.36-7.47 (m, 5H), 7.27 (d, 1H), 7.09 (t, 2H), 4.10 (t, 2H), 3.83 (s, 3H), 3.48 (t, 2H), 2.46 (s, 3H), 2.38 (m, 2H).