反应详情

To a stirred slurry of N-[2-(3,4-dichlorophenyl)-4-pentenylbutyl]-N-[(carboxymethyl)methyl]-3-cyano-2-ethyl-1-naphthamide (0.51 g) and NaIO4 (0.47 g) in 100 mL 1:1 THF:H2O was slowly added 0.32 mL OsO4 solution (4% w/w in H2O). Mixture was stirred for 18 h, 10 mL sat'd Na2S2O3(aq) was added, THF was evaporated, and aqueous residue was extracted with DCM. Extracts were dried over Na2SO4, filtered, and concentrated. This gave 0.64 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(carboxymethyl)methyl]-3-cyano-1-naphthamide after purification by chromatography (100:1, DCM:MeOH); MS: m/z 511 (M+); 1H NMR (CDCl3) δ 9.53 (s), 8.25 (s), 7.79 (d), 7.70-7.20 (m), 6.89 (d), 6.73 (d), 6.48 (dd), 4.58-4.20 (m), 3.88 (s), 3.84 (s), 3.60-3.21 (m), 3.18-2.82 (m), 2.65-2.32 (m), 1.33 (t).

1. additionwas added
2. customTHF was evaporated
3. extractionaqueous residue was extracted with DCM
4. dry with materialExtracts were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThis gave 0.64 g of N-[2-(3,4-dichlorophenyl)-4-oxobutyl]-N-[(carboxymethyl)methyl]-3-cyano-1-naphthamide after purification by chromatography (100:1, DCM:MeOH)