反应详情

A 5 g. portion of the product of Example 7 above was hydrolyzed as described above in Example 21, and the residue obtained after evaporation of the volatiles was dissolved in 300 ml. of water. Then solution was washed with 150 ml. of 15:1 diethyl ether:ethyl acetate, and was then made acid with methanesulfonic acid. The solution was then washed with 200 ml. of diethyl ether, and was degassed under vacuum and then made basic with sodium bicarbonate. The solids were collected, washed and vacuum dried to obtain 3.2 g. of crude product. The crude product was chromatographed over a 1 inch×24 inch silica gel column, eluting with a gradient composed of 2 liters of 2% methanol in chloroform phasing into 2 liters of 20% methanol in chloroform. The product-containing fractions were combined and evaporated to dryness to obtain 2.5 g. of purified product, which was characterized by its nmr spectrum (taken in dmso-d6 at 100 mHz): δ0.96 (12H, d, J=7 Hz, (CH(CH3)2)2 ; 2.72 (2H, t, J=6 Hz, NCH2); 2.96 (2H, m, J=7 Hz, (CH(CH3)2)2); 3.88 (2H, t, J=6 Hz, OCH2); 6.65 (2H, d, J=9 Hz, aromatic o to OH); 6.83 (1H, q, JH4-H5 =9 Hz, JH5-H7 =2 Hz, H5 of benzothiophene ring); 6.87 (2H, d, J=9 Hz, aromatic o to OCH2); 7.15 (2H, d, J=9 Hz, aromatic m to OH); 7.26 (1H, d, J=9 Hz, H4 of benzothiophene ring); 7.32 (1H, d, J=2 Hz, H7 of benzothiophene ring); 7.64 (2H, d, J=9 Hz, aromatic o to CO); 9.70 (2H, broad s, OH). High resolution mass spectrum: calculated for C29H31NO4S: 489.199, found 489.199; Ultraviolet spectrum λmax (ε) taken in ethanol 290 nm. (32,000); infrared absorption in KBr at 1605 cm31 1 attributable to the eneone system.

1. customthe residue obtained
2. customafter evaporation of the volatiles
3. dissolutionwas dissolved in 300 ml
4. washThen solution was washed with 150 ml
5. washThe solution was then washed with 200 ml
6. customof diethyl ether, and was degassed under vacuum
7. customThe solids were collected
8. washwashed
9. customvacuum dried
10. customto obtain 3.2 g
11. customThe crude product was chromatographed over a 1 inch×24 inch silica gel column
12. washeluting with
13. customevaporated to dryness
14. customto obtain 2.5 g
15. customabsorption in KBr at 1605 cm31 1 attributable to the eneone system