反应详情

To a cold (ice-bath) solution of 2-(2-hydroxyethyl)-5-(4-aminobenzyl)-1,5-benzothiazepine-4-one as prepared in Example 21 (0.865 g, 2.6 mM) in dry THF was added N,O-bis(trimethylsilyl)acetamide (1.16 ml, 5.2 mM). After 1 hour, 2-phenylbenzoyl chloride (0.570 g, 2.6 mM), prepared from 2-biphenylcarboxylic acid as described in Example 3, was added and stirring was continued for an addition hour. Water (80 ml) was added and the mixture was extracted with ethyl acetate (2×80 ml). The organic extract was dried (MgSO4), filtered and evaporated in vacuo to give a crude product. Purification by flash column chromatography (EM silica gel 60; 30% EtOAc in CH2Cl2) yielded the desired product as a white solid (1.1 g, 83%) m.p.116-120° C. 1H NMR (300 MHz, DMSOd6) δ7.8 (d, J=7 Hz, 1H); 5.09(d, J=15 Hz, H); 4.89(d,J=15 Hz,1H); 3.79 (m, 3H); 2.69-2.24(m, 2H); 1.71 (m, 2H); m/z (MH+)509.

1. additionwas added
2. additionwas continued for an addition hour
3. extractionthe mixture was extracted with ethyl acetate (2×80 ml)
4. extractionThe organic extract
5. dry with materialwas dried (MgSO4)
6. filtrationfiltered
7. customevaporated in vacuo
8. customto give a crude product
9. customPurification by flash column chromatography (EM silica gel 60; 30% EtOAc in CH2Cl2)