Sulfuric Acid → HCID 19737996, compound
Reaction equation
S(=O)(=O)(O)[OH:2].CO[CH:8]1[C:13]2[CH:14]=[C:15]([S:17]([NH2:20])(=[O:19])=[O:18])[S:16][C:12]=2[S:11](=[O:22])(=[O:21])[N:10]([CH3:23])[CH2:9]1.[C:24](#[N:26])[CH3:25]>>[C:24]([NH:26][CH:8]1[C:13]2[CH:14]=[C:15]([S:17]([NH2:20])(=[O:18])=[O:19])[S:16][C:12]=2[S:11](=[O:21])(=[O:22])[N:10]([CH3:23])[CH2:9]1)(=[O:2])[CH3:25]Participants
4
Procedure
To sulfuric acid (5.0 g) cooled to 0° C. was added the product from Step E (1.10 g, 3.81 mmol) dissolved in acetonitrile (35 mL) dropwise over 10 min. The mixture was stirred at ambient temperature for 2.5 days and quenched by the addition of ice and ammonium hydroxide to adjust the pH to 10. The acetonitrile was evaporated and the white precipitate was filtered and dried to give 0.41 g of the desired product. The filtrate was extracted with ethyl acetate. Evaporation to dryness gave an additional 0.33 g of the desired product (total yield 57%). Crystallization from methanol-methylene chloride gave colorless crystals: mp 252°-253° C.