反应详情

3-Chloroperbenzoic acid (43 mg, 0.177 mmol) was added to the compound of step 1 (35 mg, 0.059 mmol) in DCM (2 ml) and saturated aqueous sodium hydrogencarbonate solution (2 ml). The mixture was stirred for 30 min at room temperature and then partitioned between EA and a sodium carbonate solution. The aqueous phase was extracted with EA and the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue (44 mg) was dissolved in a mixture of 0.5 ml of THF and 1 ml of methanol. Disodium hydrogenphosphate (40 mg, 0.28 mmol) and sodium mercury amalgam (5% sodium) (250 mg) were added and the mixture was stirred for 30 min at room temperature and stored for 6 days at 5° C. Then the mixture was partitioned between 2 N hydrochloric acid and EA, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium chloride, decanted and evaporated to dryness. The residue was purified by silica gel chromatography (DCM/methanol/28% ammonia gradient, 90:10:1 to 85:15:1.5). The product fractions were evaporated to dryness and the residue partitioned between 2 N hydrochloric acid and EA. The aqueous phase was extracted with EA, and the combined organic extracts were dried over sodium chloride, decanted and evaporated to dryness.

1. custompartitioned between EA
2. extractionThe aqueous phase was extracted with EA
3. dry with materialthe combined organic phases were dried over sodium sulfate
4. customevaporated to dryness
5. dissolutionThe residue (44 mg) was dissolved in a mixture of 0.5 ml of THF and 1 ml of methanol
6. stirringthe mixture was stirred for 30 min at room temperature
7. waitstored for 6 days at 5° C
8. customThen the mixture was partitioned between 2 N hydrochloric acid and EA
9. extractionthe aqueous phase extracted with EA
10. dry with materialthe combined organic extracts were dried over sodium chloride
11. customdecanted
12. customevaporated to dryness
13. customThe residue was purified by silica gel chromatography (DCM/methanol/28% ammonia gradient, 90:10:1 to 85:15:1.5)
14. customThe product fractions were evaporated to dryness
15. customthe residue partitioned between 2 N hydrochloric acid and EA
16. extractionThe aqueous phase was extracted with EA
17. dry with materialthe combined organic extracts were dried over sodium chloride
18. customdecanted
19. customevaporated to dryness